Chlorotrimethylsilane → HCID 18651330, compound

HRID 1591058Notes

Reaction equation

HRID 1591058 reaction equation
[I:1][CH2:2][CH2:3][C@H:4]([OH:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:13][Si:14](Cl)([CH3:16])[CH3:15]>C(Cl)Cl>[I:1][CH2:2][CH2:3][C@H:4]([O:12][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 18651328HCID 18651328, compound

Product 1

HCID 18651330HCID 18651330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-iodo-3(R)-decanol (490 mg) in methylene chloride (10 ml) was added trimethylsilyl chloride (336 mg) and N-ethyldiiosopropylamin (398 mg). After stirring for 1 hour, the mixture was washed with phosphate buffer (pH 6.5, 0.066M, 10 ml) and brine (10 ml), dried and evaporated in vacuo. The residue was purified by chromatography (silica gel, 20 g, methylene chloride as eluent) to give the title compound as an oil, δ (300 MHz) 0.13 (9H, s), 0.87 (3H, t), 1.15-1.50 (12H, m), 1.92 (2H, m), 3.21 (2H, m) and 3.70 (1H, m).

Workup

  1. washthe mixture was washed with phosphate buffer (pH 6.5, 0.066M, 10 ml) and brine (10 ml)
  2. customdried
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography (silica gel, 20 g, methylene chloride as eluent)

Sources & evidence

ORD record
ord-787c027bcf80432da1ce1ba1d036916a
Source dataset
uspto-grants-1993_04
Patent number
US05206229

Reaction notes

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