Hydrochloric Acid → Ethyl 4-hydroxybicyclo[5.1.0]octane-8-carboxylate

HRID 16228Notes

Reaction equation

HRID 16228 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:13]2[CH:7]1[CH2:8][CH2:9][CH:10]([O:14][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:11][CH2:12]2)=[O:5])[CH3:2].Cl>C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH:13]2[CH:7]1[CH2:8][CH2:9][CH:10]([OH:14])[CH2:11][CH2:12]2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 686886034-(Tert-butyl-diphenyl-silanyloxy)-bicyclo[5.1.0]octane-8-carboxylic acid ethyl ester

Product 1

HCID 66665106Ethyl 4-hydroxybicyclo[5.1.0]octane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 8D (2.2 g, 5.0 mmoles) was taken in ethanol (8 mL) and 12M HCl (1 mL) was added. The reaction was stirred at room temperature for twelve hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (hexanes; ethyl acetate 100:0 to 50:50) to obtain the titled compound as a mixture of diastereomers.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (hexanes; ethyl acetate 100:0 to 50:50)

Sources & evidence

ORD record
ord-987490cbc12d43589b8c4a55fab12de9
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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