Water → (1-Allyl-3-methylcyclobutoxy)(tert-butyl)dimethylsilane

HRID 20051Notes

Reaction equation

HRID 20051 reaction equation
[CH2:1]([C:4]1([OH:9])[CH2:7][CH:6]([CH3:8])[CH2:5]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.O([Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])S(C(F)(F)F)(=O)=O.O>C(Cl)Cl>[CH2:1]([C:4]1([O:9][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:7][CH:6]([CH3:8])[CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 673052351-Allyl-3-methylcyclobutanol

Product 1

HCID 67304682(1-Allyl-3-methylcyclobutoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Allyl-3-methylcyclobutanol (2.25000 g, 17.8 mmol) (the 4:1 mixture of cis/trans-isomers) was dissolved in 50 ml of CH2Cl2 and DIEA (5.59 ml, 32.1 mmol) and tert-butyldimethylsilyl triflate (5.73 ml, 25.0 mmol) were added. The mixture was stirred for 2 h and hydrolyzed with water, extracted with 200 ml Et2O (3×each), dried over MgSO4 and evaporated. Glass col. chrom. (10-30% EtOAc in Hex.) provided (1-allyl-3-methylcyclobutoxy)(tert-butyl)dimethylsilane as a yellow oil. Mixture of cis/trans at the cyclobutylring (4:1)

Workup

  1. extractionextracted with 200 ml Et2O (3×each),
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-3e8ca5f8caa8475b9eebf63e5beb0ffd
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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