2-Cyclopentene-1-carboxylicacid,4-hydroxy-1-methyl-,methylester(9CI)

Base Information

Chemical Name:2-Cyclopentene-1-carboxylicacid,4-hydroxy-1-methyl-,methylester(9CI)
CAS No.:249537-10-8
Molecular Formula:C₈H₁₂O₃
Molecular Weight:156.181
Hs Code.:
Mol file:249537-10-8.mol

Synonyms:2-Cyclopentene-1-carboxylicacid,4-hydroxy-1-methyl-,methylester(9CI)

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Chemical Property of 2-Cyclopentene-1-carboxylicacid,4-hydroxy-1-methyl-,methylester(9CI)

Chemical Property:

Boiling Point:219.6±40.0 °C(Predicted)
PKA:14.21±0.40(Predicted)
Density:1.156±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

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Technology Process of 2-Cyclopentene-1-carboxylicacid,4-hydroxy-1-methyl-,methylester(9CI)

There total 18 articles about 2-Cyclopentene-1-carboxylicacid,4-hydroxy-1-methyl-,methylester(9CI) 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: 42.0%

: 249536-82-1
methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate

: 206755-01-3,249537-15-3
methyl (1S,2S)-2-hydroxy-1-methyl-3-cyclopentenecarboxylate

: 206755-02-4,249537-10-8
methyl (1S,4S)-4-hydroxy-1-methyl-2-cyclopentenecarboxylate

Guidance literature:: methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate; With dichloro bis(acetonitrile) palladium(II); p-benzoquinone; In tetrahydrofuran; Heating;

With methanol; potassium carbonate; at 20 ℃; for 1h;
DOI:10.1248/cpb.47.1256

Reference yield:

: 249536-97-8
methyl (1S,4S)-4-acetoxy-1-methyl-2-cyclopentenecarboxylate

: 206755-02-4,249537-10-8
methyl (1S,4S)-4-hydroxy-1-methyl-2-cyclopentenecarboxylate

Guidance literature:: With methanol; potassium carbonate; Yield given;
DOI:10.1016/S0957-4166(98)00065-2

Reference yield:

: 139616-47-0
methyl (1S)-2-((1R,2R)-2-hydroxycycloheptan-1-yl)oxy-1-methyl-2-cyclopenten-1-carboxylate

: 206755-02-4,249537-10-8
methyl (1S,4S)-4-hydroxy-1-methyl-2-cyclopentenecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / I₂; Et₃N / tetrahydrofuran / 24 h / -40 - -20 °C

2.1: 94 percent / DBU / 1 h / 95 - 100 °C

3.1: 85 percent / 10 percent aq. HCl / methanol / 8 h / 20 °C

4.1: 86 percent / NaBH₄; CeCl₃ / methanol / 0.25 h / -40 °C

5.1: 100 percent / 4-DMAP; pyridine / 1 h / 20 °C

6.1: 1,4-benzoquinone; PdCl₂(MeCN)2 / tetrahydrofuran / Heating

6.2: 42 percent / K₂CO₃; MeOH / 1 h / 20 °C

With pyridine; hydrogenchloride; dmap; dichloro bis(acetonitrile) palladium(II); sodium tetrahydroborate; cerium(III) chloride; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-benzoquinone; In tetrahydrofuran; methanol; 1.1: Iodination / 2.1: Elimination / 3.1: Hydrolysis / 4.1: Luche reduction / 5.1: Acetylation / 6.1: Rearrangement / 6.2: methanolysis;
DOI:10.1248/cpb.47.1256