Water → 1-Allyl-3-methylcyclobutanol

HRID 20050Notes

Reaction equation

HRID 20050 reaction equation
C[CH:2]1[CH2:5][CH2:4][C:3]1=[O:6].[CH2:7]([Mg]Br)[CH:8]=[CH2:9].O.[CH2:13]1COCC1>>[CH2:7]([C:3]1([OH:6])[CH2:2][CH:5]([CH3:13])[CH2:4]1)[CH:8]=[CH2:9]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 151992-Methylcyclobutan-1-oneHCID 178455850HCID 178455850, compound

Product 1

HCID 673052351-Allyl-3-methylcyclobutanolYield 46.9%

Procedure

Methylcyclobutanone (3.200 g, 38.043 mmol) was dissolved in 200 ml THF and allylmagnesium bromide (190.21 ml, 190.21 mmol) was added in one portion. The mixture was stirred for 4 h at RT, hydrolyzed with water and extracted. The combined organic extracts were dried over MgSO4 and evaporated and purified via glass col. Chrom. (25-75% hex. in EtOAc). 1-Allyl-3-methylcyclobutanol (2.250 g, 46.9% yield) was obtained as a mixture of cis-trans isomers approx 4:1 (where the major compound is the one Me-cis to OH) based on NMR.

Workup

  1. extractionextracted
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customevaporated
  4. custompurified via glass col

Sources & evidence

ORD record
ord-5a21bab2a39b4e56a4ba1ff98b5872cb
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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