Triethylamine → HCID 86747280, compound

HRID 1735183Notes

Reaction equation

HRID 1735183 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Si:13](/[CH:20]=[CH:21]/[CH2:22][OH:23])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>ClCCl>[Si:13](/[CH:20]=[CH:21]/[CH2:22][OH:23])([C:16]([CH3:18])([CH3:19])[CH3:17])([CH3:15])[CH3:14].[CH3:8][S:9]([O-:11])(=[O:23])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11829925HCID 11829925, compound

Product 1

HCID 86747280HCID 86747280, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

As for the preparation described in Example 39, 1.6 ml (11.4 mmol) of triethylamine and 0.74 ml (9.55 mmol) of methanesulfonylchloride in 15 ml of dry dichloromethane are added to 1.3 g (7.6 mmol) of (E)-3-(t-butyldimethylsilyl)-2-propen-1-ol. [Lipshutz et al., J. Org. Chem. 54(21), 4975 (1989)] in 20 ml of dry dichloromethane to give after purification by flash chromatography on silica gel and elution with petroleum ether:ethyl acetate 9:1 1.3 g (67%) of expected (E)-3-(t-butyldimethylsilyl)-2-propen-1-ol, methanesulfonate as a colorless liquid.

Workup

  1. customafter purification by flash chromatography
  2. washon silica gel and elution with petroleum ether:ethyl acetate 9:1 1.3 g (67%) of expected (E)-3-(t-butyldimethylsilyl)-2-propen-1-ol, methanesulfonate as a colorless liquid

Sources & evidence

ORD record
ord-5e42ece7164f47fdb251e2fe800cfab0
Source dataset
uspto-grants-1996_07
Patent number
US05536732

Reaction notes

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