4-Chloro-alpha-cyclopropyl-alpha-methylbenzenemethanol → alpha-Cyclopropyl-2,3-dihydro-alpha-methyl-1,4-benZodioxin-6-methanol

HRID 561466Notes

Reaction equation

HRID 561466 reaction equation
[CH3:1][C:2]([C:4]1[CH:13]=[CH:12][C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)=[O:3].[CH:14]1([Mg]Br)[CH2:16][CH2:15]1.C1(C(C2C=CC(Cl)=CC=2)(O)C)CC1>O1CCCC1>[CH:14]1([C:2]([C:4]2[CH:13]=[CH:12][C:7]3[O:8][CH2:9][CH2:10][O:11][C:6]=3[CH:5]=2)([OH:3])[CH3:1])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 234634-Chloro-alpha-cyclopropyl-alpha-methylbenzenemethanolHCID 761431,4-Benzodioxan-6-yl methyl ketoneHCID 178418630HCID 178418630, compound

Product 1

HCID 58392439alpha-Cyclopropyl-2,3-dihydro-alpha-methyl-1,4-benZodioxin-6-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared starting from 1.50 g (8.42 mmol) of 1,4-benzodioxan-6-yl methyl ketone and 33.7 ml (16.84 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran in analogy to the synthesis of the compound from Example 138A. 1.12 g (59% of theory) of the title compound were obtained.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-1cc945a37750462c96a318d87a9744c5
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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