4-Chloro-alpha-cyclopropyl-alpha-methylbenzenemethanol → 1-Cyclopropyl-1-(2,2-difluoro-1,3-benzodioxol-5-yl)ethanol

HRID 561468Notes

Reaction equation

HRID 561468 reaction equation
[F:1][C:2]1([F:14])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11](=[O:13])[CH3:12])=[CH:10][C:4]=2[O:3]1.[CH:15]1([Mg]Br)[CH2:17][CH2:16]1.C1(C(C2C=CC(Cl)=CC=2)(O)C)CC1>O1CCCC1>[CH:15]1([C:11]([C:9]2[CH:8]=[CH:7][C:5]3[O:6][C:2]([F:1])([F:14])[O:3][C:4]=3[CH:10]=2)([OH:13])[CH3:12])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 234634-Chloro-alpha-cyclopropyl-alpha-methylbenzenemethanolHCID 269852185-Acetyl-2,2-difluoro-1,3-benzodioxoleHCID 178418630HCID 178418630, compound

Product 1

HCID 583925051-Cyclopropyl-1-(2,2-difluoro-1,3-benzodioxol-5-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared starting from 0.75 g (3.75 mmol) of 1-(2,2-difluoro-1,3-benzodioxol-5-yl)ethanone and 15.0 ml (7.50 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran in analogy to the synthesis of the compound from Example 138A. 0.67 g (74% of theory) of the title compound was obtained.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ee4b4eddab094b08a50098e86105b3cc
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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