Trifluoroacetic acid → (1R,2R)-ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate

HRID 471432Notes

Reaction equation

HRID 471432 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C(C)(C)C)=[CH:11][CH:10]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72700305(1R,2R)-2-(4-tert-Butoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 71114948(1R,2R)-ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylateYield 66.8%

Procedure

(1R,2R)-2-(4-tert-Butoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester (5.9 g, 22.5 mmol) is cooled to 0° C. and trifluoroacetic acid (14 mL, 182.5 mmol) is added. The mixture is stirred for 5 minutes and then concentrated under vacuum. The residue is reevaporated 3 times from dichloromethane then purified by flash chromatography (0-10% ethyl acetate in cyclohexane) to give the title compound (yield 3.10 g).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue is reevaporated 3 times from dichloromethane
  3. customthen purified by flash chromatography (0-10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-f6d233f571cf45309a00cfddc5eab758
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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