(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

Base Information

Chemical Name:(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol
CAS No.:70913-22-3
Molecular Formula:C₁₉H₂₄O₂
Molecular Weight:284.398
Hs Code.:

Synonyms:(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

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Chemical Property of (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

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Technology Process of (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

There total 19 articles about (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 68241-54-3
(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone

: 70913-22-3
(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Yield given;
DOI:10.1021/jo00151a016

Reference yield:

: 100-39-0
benzyl bromide

: 70913-22-3
(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

Guidance literature:: Multi-step reaction with 17 steps

1: 87 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 12 h

2: p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

3: 89 percent / 10percent aq. KOH / methanol / 21 h / 55 °C

4: 64 percent / p-toluenesulfonyl chloride, DBU / toluene / 1.) 0 deg C, 15 min, 2.) ambient temperature, 1 h

5: 92 percent / DBU / toluene / 3 h / Heating

6: i-Bu₂AlH / toluene / 0.5 h / -78 °C

7: benzene / 1 h / Ambient temperature

8: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

9: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

10: 1.5percent KOH / methanol / 8 h / Ambient temperature

11: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

12: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

13: 96 percent / pyridine / 2 h / Ambient temperature

14: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

15: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

16: DBU / benzene / 0.25 h / Ambient temperature

17: LiAlH₄

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; Collins oxidation agent; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone; toluene; benzene;
DOI:10.1021/ja00379a030

Reference yield:

: 71686-31-2
(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

: 70913-22-3
(1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol

Guidance literature:: Multi-step reaction with 11 steps

1: benzene / 1 h / Ambient temperature

2: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

3: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

4: 1.5percent KOH / methanol / 8 h / Ambient temperature

5: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

6: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

7: 96 percent / pyridine / 2 h / Ambient temperature

8: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

9: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

10: DBU / benzene / 0.25 h / Ambient temperature

11: LiAlH₄

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; Collins oxidation agent; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; benzene;
DOI:10.1021/ja00379a030