Trimethylsilyl triflate → 2-[3-Bromo-4-(cyclopropylmethoxy)phenyl]-2-methyl-1,3-dioxolane

HRID 2208137

Reaction equation

HRID 2208137 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C[Si](C)(C)[O:30][CH2:31][CH2:32]O[Si](C)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2([CH3:14])[O:30][CH2:31][CH2:32][O:15]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 629080041-[3-Bromo-4-(cyclopropylmethoxy)phenyl]ethanone

Product 1

HCID 670330682-[3-Bromo-4-(cyclopropylmethoxy)phenyl]-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-bromo-4-cyclopropylmethoxy-phenyl)-ethanone from example B.b13 (14.0 g; 52.0 mmol) in dry dichloromethane (250 mL) was cooled in an ice-bath before addition of trimethylsilyl trifluoro-methane sulfonate (0.23 g; 1.04 mmol) and dropwise addition of 1,2-bis(trimethylsilyloxy)-ethane (13.15 g; 62.4 mmol). The reaction mixture was stirred for two hours, extracted with 1M aqueous NaHCO3 (100 mL) and dried over MgSO4. The crude is purified by column chromatography on silica gel (ethyl acetate/cyclohexane-9:1) to yield the title compound as pale yellow oil.

Workup

  1. extractionextracted with 1M aqueous NaHCO3 (100 mL)
  2. dry with materialdried over MgSO4
  3. customThe crude is purified by column chromatography on silica gel (ethyl acetate/cyclohexane-9:1)

Sources & evidence

ORD record
ord-cce35a5fc1f14c97afa03aa8fb964833
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Linked notes

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