A Modified Synthesis of Oxetan-3-ol

Article abstract of DOI:10.1134/S107042802005022X

Abstract: A highly regioselective ring opening reaction of terminal epoxides with 2-bromobenzoic acid catalyzed by tetrabutylammonium bromide was accomplished. The procedure is operationally simple and practical for the synthesis of a series of β-hydroxy esters. Using this protocol, oxetan-3-ol could be prepared efficiently in a good yield.

Full text of DOI:10.1134/S107042802005022X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 5, pp. 877–883. © Pleiades Publishing, Ltd., 2020.
A Modified Synthesis of Oxetan-3-ol
X. Y. Xiaa, W. Suna, W. Hea, Y. Fenga, L. Zhana, and Y. Luoa,*
a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development,
School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241 China
*e-mail: yluo@chem.ecnu.edu.cn
Received October 31, 2019; revised January 20, 2020; accepted January 28, 2020
Abstract—A highly regioselective ring opening reaction of terminal epoxides with 2-bromobenzoic acid cata-
lyzed by tetrabutylammonium bromide was accomplished. The procedure is operationally simple and practical
for the synthesis of a series of β-hydroxy esters. Using this protocol, oxetan-3-ol could be prepared efficiently in
a good yield.
Keywords: β-hydroxy esters, 2-bromobenzoic acid, epoxide, epichlorohydrin, oxetan-3-ol
DOI: 10.1134/S107042802005022X
Terminal epoxides are versatile substrates in organic
synthesis because of the easy synthesis and ability to
undergo ring opening reactions under the action of
various nucleophiles [1]. Among such reactions, the
reaction of carboxylic acids with terminal epoxides
has attracted special attention [2], since it provides a
convenient synthetic approach to 1,2-diol monoesters
[3–4].
still calls for further investigations [12–14], because in
some works the regioselectivity was not good enough,
while in other works, insufficient regioselectivity data
were reported [15, 16].
Recently, in an effort to develop a practical synthetic
protocol for oxetan-3-ol (1), we obtained better results
in the ring opening reactions of epichlorohydrin with
benzoic acids, because the benzoyloxy groups were
less prone to isomerization and migration to the vicinal
hydroxy group [17, 18]. Herein, we report the results of
detailed investigations into the synthesis of this building
block.
Many β-hydroxy esters are crucial precursors for
the synthesis of natural products, pharmaceuticals, and
fragrances [5–9]. For instance, oxetan-3-ol (1), a popular
moiety in pharmaceutical industry, could be prepared
from a β-hydroxy ester intermediate via ring opening in
epichlorohydrin (Scheme 1) [10, 1]. Although several
works have published on ring opening reaction in
terminal epoxides with carboxylic acids, this reaction
First we selected the reaction of 2-chlorobenzoic
acid with epichlorohydrin as a model reaction
(Table 1). We examined the effect of different phase–
Scheme 1.
OH
OH
O
Cl
O
Cl
O
O
main product
oxetan-3-ol (1)
O
O
HO
Cl
by product
-
877

878
XIA et al.
Table 1. Screening of catalysts and solvents for ring opening in epichlorohydrin
2a–4a
2b–4b
R = Cl (2a, 2b), Br (3a, 3b), H (4a, 4b).
Entry no.
Product no.
2a/2b
Catalyst
–
Solvent
EtOAc
CH3CN
DMF
Total yield, %
Regioisomeric ratio (a/b)
1
2
3
4
5
6
7
8
No reaction
–
2a/2b
TBAB
TBAB
TBAB
TBAC
TEBAC
TBAB
TBAB
74
84
86
80
77
93
87
>99/1
>99/1
>99/1
>99/1
>99/1
>99/1
5.8/1
2a/2b
2a/2b
EtOAc
EtOAc
EtOAc
EtOAc
EtOAc
2a/2b
2a/2b
3a/3b
4а/4b
transfer catalysts, including tetrabutylammonium bro-
mide (TBAB), tetrabutylammonium chloride (TBAC),
and benzyltriethylammonium chloride (TEBAC). As
seen from Table 1, the reaction did not occur in the
absence of a catalyst (Table 1, entry 1). As a remarkable
advantage of our approach one can notice a dramatically
reduced degree of isomerization, which can be associated
with enhanced steric hindrance (Table 1, entries
2–7). However, the regioselectivity of the reaction
with benzoic acid proved to be not so high (Table 1,
entry 8). The best results were obtained with 1.1 equiv
of 2-bromobenzoic acid, 5 mol % TBAB as the catalyst,
and ethyl acetate as the solvent (Table 1, entry 7).
was another key step in the synthesis of oxetan-3-ol
(1), which had to be optimized. To develop an efficient
cyclization protocol, different bases and solvents were
screened (Table 3). As seen from the Table 3, oxetane
13 was obtained in low yields in aprotic solvents, such
as THF and DMF (entries 1, 2, and 10). Among the five
protic solvents tested, t-BuOH usually gave better yields.
Furthermore, among the five bases tested, t-BuONa
and t-BuOK were more efficient that the other bases
(Table 3, entries 8 and 11). We gave preference to
t-BuONa, because it was cheaper than t-BuOK.
Finally, 3-(1-ethoxyethoxy)oxetane (13) was hyd-
rolyzed with water in the presence of a catalytic amount
of toluenesulfonic acid to obtain oxetan-3-ol (1) in 77%
yield.
To explore the scope of the proposed protocol, a
variety of epoxides were reacted with 2-bromobenzoic
acid in the optimal conditions (Table 2). As seen,
satisfactory yields were obtained with all the tested
terminal epoxides.
In conclusion, we developed an improved and facile
five-step synthesis of oxetan-3-ol (1) with a total yield
of 50%.
Thus, a modified synthesis of oxetan-3-ol (1) could be
developed. As the next step, 3-chloro-2-hydroxypropyl
2-bromobenzoate (3a) was treated with ethyl vinyl ether
to obtain compound 11 (yield 85%) (Scheme 2). The
subsequent hydrolysis of the latter gave alcohol 12 in a
yield of 90%. However, we further found that cyclization
EXPERIMENTAL
Commercial reagents were used without further
purification. The IR spectra were run on a Bruker Tensor
1
27 FTIR spectrometer. The H NMR spectra were
recorded on Bruker DRX-400 (400 MHz) or Bruker
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A MODIFIED SYNTHESIS OF OXETAN-3-OL
Table 2. Epoxide ring opening with 2-bromobenzoic acid
879
Entry no.
Epoxide
Product
Comp. no.
Yield, %
1
5
87
83
85
2
3
6
7
4
8
89
O
8
9
9
83
88
OTBS
O
10
O
Scheme 2.
O
O
p-TsOH
DCM, 85%
O
Cl
+
O
Cl
O
O
O
OH
HO
Br
Br
3a
11
Cl
O
OH
KOH
MeOH/H2O, 90%
O
p-TsOH
t-BuONa
t-BuOH, 92%
O
O
H2O, 77%
O
O
12
13
1
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880
XIA et al.
Table 3. Effect of bases and solvents on the cyclization of alcohol 12 into oxetane 13
Entry no.
Base
NaH
Solvent
THF
T, °C
65
80
70
70
70
70
70
70
70
65
70
70
Yield, %
24
1
2
NaH
DMF
28
3
EtONa
EtONa
NaOH
EtOH
62
4
t-BuOH
MeOH
EtOH
65
5
51
6
NaOH
48
7
NaOH
t-BuOH
t-BuOH
EtOH
45
8
t-BuOK
t-BuOK
t-BuONa
t-BuONa
t-BuONa
90
9
74
10
11
12
THF
38
t-BuOH
EtOH
92
77
DRX-500 (500 MHz) spectrometers. The 13C NMR
spectra were obtained on a JNM-EX400 (100 MHz)
spectrometer. The chemical shifts were measured in
ppm relative to TMS. The high-resolution mass spectra
(ESI) were obtained on a Bruker MicroTof II mass
spectrometer.
m/z: 272.9880 [M (35Cl, 37Cl) + Na]+. Calculated, m/z:
272.9875.
3-Chloro-2-hydroxypropyl 2-bromobenzoate (3a)
was prepared following the general procedure using
2-bromobenzoic acid. Yield 5.25 g (93%), oil. 1H NMR
spectrum (500 MHz, CDCl3), δ, ppm: 2.80 br.s (1H,
OH), 3.70–3.77 m (2H, CH2Cl), 4.22–4.25 m (1H,
CH), 4.45–4.50 m (2H, OCH2), 7.35–7.41 m (2Harom),
7.67–7.68 m (1Harom), 7.81–7.83 m (1Harom). 13C NMR
spectrum (126 MHz, CDCl3), δ, ppm: 44.1, 64.4, 65.0,
121.7, 127.2, 131.4, 132.8, 134.4, 134.4, 165.8. Mass-
spectrum, found, m/z: 314.9394 [M (35Cl, 79Br) + Na]+.
C10H10O3BrClNa. Calculated, m/z: 314.9394. Found,
m/z: 316.9369 [M (37Cl, 79Br) + Na]+. Calculated, m/z:
316.9374. Found, m/z: 318.9345 [M (37Cl, 81Br) + Na]+.
Calculated, m/z: 318.9344.
Ring opening in epichlorohydrin (general
procedure). Epichlorohydrin (21.2 mmol) and TBAB
(5 mol %) were added to a solution of carboxylic
acid (19.2 mmol) in EtOAc. The reaction mixture
was refluxed at 65°C for 4 h and then cooled down to
room temperature and washed with a saturated Na2CO3
solution. The organic layer was dried over anhydrous
Na2SO4 and evaporated to dryness, and the product was
purified by column chromatography on silica gel, eluent
petroleum ether–ethyl acetate, 5 : 10.
3-Chloro-2-hydroxypropyl benzoate (4a) was pre-
pared following the general procedure using benzoic
acid. Yield 3.58 g (87%), oil. 1H NMR spectrum
(500 MHz, CDCl3), δ, ppm: 2.91 br.s (1H, OH),
3.63–3.73 m (2H, CH2Cl), 4.19–4.22 m (1H, CH), 4.44–
4.48 m (2H, OCH2), 7.41–7.45 m (2Harom), 7.54–7.58 m
(1Harom), 8.01–8.04 m (2Harom).
3-Chloro-2-hydroxypropyl 2-chlorobenzoate (2a)
was prepared following the general procedure using
2-chlorobenzoic acid. Yield 4.10 g (86%), oil. 1H NMR
spectrum (500 MHz, CDCl3), δ, ppm: 2.71 br.s (1H,
OH), 3.69–3.76 m (2H, CH2Cl), 4.22–4.23 m (1H,
CH), 4.47–4.48 m (2H, OCH2), 7.32–7.35 m (1Harom),
7.42–7.47 m (2Harom), 7.84–7.86 m (1Harom). 13C NMR
spectrum (126 MHz, CDCl3), δ, ppm: 45.9, 66.1, 69.4,
126.7, 129.4, 131.1, 131.7, 133.1, 133.6, 165.6. Mass-
spectrum, found, m/z: 270.9912 [M (35Cl, 35Cl) + Na]+.
C10H10O3Cl2Na. Calculated, m/z: 270.9905. Found,
2-Hydroxybutyl 2-bromobenzoate (5) was prepa-
red following the general procedure from 2-bromoben-
zoic acid (5.97 mmol), 1,2-epoxybutane (4.85 mmol),
and TBAB (0.34 mmol). Yield 1.18 g (87%), oil. IR
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 5 2020

A MODIFIED SYNTHESIS OF OXETAN-3-OL
881
spectrum, ν, cm–1: 2966, 2873, 1722, 1249. H NMR
spectrum (500 MHz, CDCl3), δ, ppm: 0.94–1.02 m (3H,
CH2CH3), 1.56–1.59 m (2H, CH2CH3), 2.27 br.s (1H,
OH), 3.88–3.92 m (1H, CH), 4.17–4.41 m (2H, OCH2),
7.26–7.37 m (2Harom), 7.62–7.64 m (1Harom), 7.77–
7.79 m (1Harom). 13C NMR spectrum (126 MHz, CDCl3),
δ, ppm: 8.8, 25.3, 68.5, 70.1, 120.4, 126.3, 130.5,
131.1, 131.7, 133.3, 165.3. Mass-spectrum, found, m/z:
294.9935 [M (79Br) + Na]+. C11H13O3BrNa. Calculated,
m/z: 294.9940. Found, m/z: 296.9901 [M (81Br) + Na]+.
Calculated, m/z: 296.9919.
(4.16 mmol), and TBAB (0.29 mmol). Yield 1.2 g
1
(89%), oil. IR spectrum, ν, cm–1: 3060, 2939, 1717,
1
1249. H NMR spectrum (400 MHz, CDCl3), δ, ppm:
2.20 br.s (1H, OH), 3.84–3.94 m (2H, CH2), 6.01–
6.02 m (1H, CH), 7.22–7.39 m (7Harom), 7.58 d (1Harom
,
J 7.4 Hz), 7.76 d (1Harom, J 7.2 Hz). 13C NMR spectrum
(126 MHz, CDCl3), δ, ppm: 65.2, 77.7, 120.9, 126.1,
126.6, 127.8, 128.0, 131.0, 131.3, 132.1, 133.7, 135.9,
164.9. Mass-spectrum, found, m/z: 342.9920 [M (79Br) +
Na]+. C15H13O3BrNa. Calculated, m/z: 342.9940. Found,
m/z: 344.9910 [M (81Br) + Na]+. Calculated, m/z:
344.9920.
2-Hydroxy-3-(propanoyloxy)propyl 2-bromoben-
zoate (6) was prepared following the general
procedure from 2-bromobenzoic acid (4.97 mmol),
2,3-epoxypropyl propanoate (4.15 mmol), and TBAB
(0.29 mmol). Yield 1.14 g (83%), oil. IR spectrum,
3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxy-
propyl 2-bromobenzoate (9) was prepared following
the general procedure from 2-bromobenzoic acid
(7.46 mmol), tert-butyldimethylsilyl glycidyl ether
(6.37 mmol), and TBAB (0.45mmol). Yield 2.04 g
(83%), oil. IR spectrum, ν, cm–1: 2958, 2851, 1718, 1243.
1H NMR spectrum (400 MHz, CDCl3), δ, ppm: 0.08–
0.10 m [6H, Si(CH3)2], 0.91–0.92 m [9H, C(CH3)3],
2.65 br.s (1H, OH), 3.73–3.77 m (2H, OCH2), 3.97–
4.11 m (1H, CH), 4.38–4.42 m (2H, OCH2), 7.31–
7.42 m (2Harom), 7.66 d (1Harom, J 7.4 Hz), 7.79–
7.85 m (1Harom). 13C NMR spectrum (126 MHz, CDCl3),
δ, ppm: –4.85, 18.8, 26.4, 64.4, 66.8, 70.4, 122.2, 127.8,
132.1, 132.6, 133.3, 134.9, 166.8. Mass-spectrum, found,
m/z: 411.0580 [M (79Br) + Na]+. C16H25O4BrNaSi.
Calculated, m/z: 411.0598. Found, m/z: 413.0544
[M (81Br) + Na]+. Calculated, m/z: 413.0577.
1
ν, cm–1: 2983, 1728, 1293, 1243. H NMR spectrum
(500 MHz, CDCl3), δ, ppm: 1.11–1.15 m (3H,
CH2CH3), 2.35–2.40 m (2H, CH2CH3), 3.02 br.s (1H,
OH), 4.23–4.45 m (5H, CH2CHCH2), 7.33–7.38 m
(2Harom), 7.64–7.66 m (1Harom), 7.80–7.82 m (1Harom).
13C NMR spectrum (126 MHz, CDCl3), δ, ppm: 9.0,
27.4, 65.1, 66.2, 68.0, 121.6, 127.3, 131.5, 131.6,
132.9, 134.4, 166.1, 174.6. Mass-spectrum, found, m/z:
352.9977 [M (79Br) + Na]+. C15H15O5BrNa. Calculated,
m/z: 352.9995. Found, m/z: 354.9952 [M (81Br) + Na]+.
Calculated, m/z: 354.9975.
3-{[tert-Butyl(diphenyl)silyl]oxy}-2-hydroxy-
propyl 2-bromobenzoate (7) was prepared following
the general procedure from 2-bromobenzoic acid
(5.72 mmol), tert-butyl(oxiran-2-ylmethoxy)diphenyl-
silane (4.80 mmol), and TBAB (0.34 mmol). Yield
2.10 g (85%), oil. IR spectrum, ν, cm–1: 3071, 2928,
2-Hydroxy-3-phenoxypropyl 2-bromobenzoate
(10) was prepared following the general procedure from
2-bromobenzoic acid (7.03 mmol), 2-(phenoxymethyl)-
oxirane (5.85 mmol), and TBAB (0.41 mmol). Yield
1.80 g (88%), oil. IR spectrum, ν, cm–1: 2935, 2884,
1
1728, 1243. H NMR spectrum (400 MHz, CDCl3),
1
δ, ppm: 1.08 s [9H, C(CH3)3], 2.59 br.s (1H, OH),
3.76–3.83 m (2H, OCH2), 4.08–4.11 m (1H, CH), 4.41–
4.47 m (2H, OCH2), 7.32–7.46 m (8Harom), 7.66–
7.67 m (5Harom), 7.73–7.76 m (1Harom). 13C NMR
spectrum (126 MHz, CDCl3), δ, ppm: 18.5, 26.1, 63.8,
65.4, 69.2, 121.0, 126.4, 127.1, 129.2, 131.0, 131.1,
132.0, 132.1, 133.6, 134.8, 165.3. Mass-spectrum, found,
m/z: 535.0920 [M (79Br) + Na]+. C26H29O4BrNaSi.
Calculated, m/z: 535.0911. Found, m/z: 537.0913
[M (81Br) + Na]+. Calculated, m/z: 537.0890.
1722, 1230. H NMR spectrum (400 MHz, CDCl3),
δ, ppm: 2.80 br.s (1H, OH), 4.13–4.16 m (2H, OCH2),
4.40–4.42 m (1H, CH), 4.53–4.61 m (2H, OCH2), 6.94–
6.96 m (2Harom), 6.99–7.02 m (1Harom), 7.28–7.33 m
(2Harom), 7.38–7.40 m (2Harom), 7.67–7.69 m (1Harom),
7.83–7.85 m (1Harom). 13C NMR spectrum (126 MHz,
CDCl3), δ, ppm: 66.4, 68.5, 68.7, 114.6, 121.4, 121.6,
127.3, 129.6, 131.6, 131.8, 132.9, 134.4, 158.3, 166.3.
Mass-spectrum, found, m/z: 373.0021 [M (79Br) + Na]+.
C16H15O4BrNa. Calculated, m/z: 373.0046. Found, m/z:
375.0000 [M (81Br) + Na]+. Calculated, m/z: 375.0025.
2-Hydroxy-2-phenylethyl 2-bromobenzoate (8)
was prepared following the general procedure from
2-bromobenzoic acid (4.97 mmol), styrene oxide
3-Chloro-2-(1-ethoxyethoxy)propyl 2-bromoben-
zoate (11). Ethyl vinyl ether (8.1 g, 110 mmol) and
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XIA et al.
toluenesulfonic acid (0.94 g, 3.75 mmol) were added to a
solution of 3-chloro-2-hydroxypropyl 2-bromobenzoate
(22 g, 75 mmol) in dichloromethane (90 mL). The
reaction mixture was stirred at room temperature for 3 h
and then washed with water (80 mL). The organic layer
was dried over anhydrous Na2SO4 and evaporated to
give 23.3 g (85%) of compound 11 as a light yellow oil.
1H NMR spectrum (400 MHz, CDCl3), δ, ppm: 1.14–
1.21 m (3H, CH2CH3), 1.33–1.37 m (3H, CHCH3),
3.64–3.73 m (4H, CH2Cl, CH2CH3), 4.16–4.18 m (1H,
CH), 4.44–4.53 m (2H, OCH2), 4.88–4.90 m (1H,
OCHO), 7.26–7.37 m (2Harom), 7.65–7.66 m (1Harom),
7.77–7.80 m (1Harom). 13C NMR spectrum (126 MHz,
CDCl3), δ, ppm: 15.2, 20.2, 44.1, 60.6, 65.0, 72.8, 99.9,
121.7, 127.2, 131.5, 131.8, 132.8, 134.4, 165.8. Mass-
spectrum, found, m/z: 386.9977 [M (35Cl, 79Br) + Na]+.
C10H9O3Cl3Na. Calculated, m/z: 386.9975. Found,
m/z: 388.9961 [M (37Cl, 79Br) + Na]+. Calculated, m/z:
388.9954. Found, m/z: 388.9946 [M (35Cl, 81Br) + Na]+.
Calculated, m/z: 388.9945. Found, m/z: 390.9930 [M
(37Cl, 81Br) + Na]+. Calculated, m/z: 390.9925.
light yellow oil. 1H NMR spectrum (500 MHz, CDCl3),
δ, ppm: 1.15–1.18 m (3H, CH2CH3), 1.27 d (3H,
CHCH3, J 5.4 Hz), 3.42–3.62 m (2H, CH2CH3), 4.63–
4.82 m (6H, 2CH2O, OCH, OCHO). 13C NMR spectrum
(126 MHz, CDCl3), δ, ppm: 15.2, 20.1, 61.2, 67.2, 79.0,
79.9, 99.2.
Oxetan-3-ol (1). p-Toluenesulfonic acid (0.2 g,
1.05 mmol) was added to a solution of compound 13
(25 g, 171 mmol) in water (10 mL). The reaction
mixture was allowed to stand at 25°C for 2 h and, after
the addition of aqueous NaHCO3 to pH 8, it was filtered.
The filtrate was evaporated to dryness, the residue was
dissolved in ethyl acetate (30 mL), and the solution was
filtered. The organic layer was dried over anhydrous
Na2SO4 and evaporated to leave a crude product, which
was distilled to obtain 9.7 g (77%) of compound 1 as
1
a colorless oil. H NMR spectrum (400 MHz, CDCl3),
δ, ppm: 4.53–4.52 m (CH, OH), 4.80–4.77 m (4H,
CH2OCH2). 13C NMR spectrum (126 MHz, CDCl3),
δ, ppm: 65.0, 80.6.
ACKNOWLEDGMENTS
3-Chloro-2-(1-ethoxyethoxy)propanol (12). Com-
pound 11 (35 g, 95.7 mmol) and KOH (6.4 g,
0.11 mol) were added to a mixture of methanol (80 mL)
and water (80 mL), and the reaction mixture was allowed
to stand at room temperature for 5 h. Methanol was then
removed under reduced pressure, and the residue was
extracted with dichloromethane (100 mL) and washed
with water (100 mL). The organic layer was dried over
anhydrous Na2SO4 and evaporated to obtain 15.7 g
We are grateful to the Laboratory of Organic Functional
Molecules, Sino–French Institute of ECNU for financial
support.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
SUPPLEMENTARY MATERIALS
Supplementary materials are available for this article at
https://doi.org/10.1134/S107042802005022X and are acces-
sible for authorized users.
1
(90%) of compound 12 as a light yellow oil. H NMR
spectrum (500 MHz, CDCl3), δ, ppm: 1.23–1.26 m (3H,
CH2CH3), 1.38 d (3H, CHCH3, J 5.3Hz), 1.76 br.s (1H,
OH), 3.53–3.73 m (6H, CH2OH, CH2Cl, CH2CH3),
3.85–3.88 m (1H, OCH), 4.79–4.82 m (1H, OCHO). 13C
NMR spectrum (126 MHz, CDCl3), δ, ppm: 15.2. 20.2,
43.5, 61.2, 63.2, 78.9, 101.1.
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