Triethylamine → HCID 10892715, compound

HRID 1612935Notes

Reaction equation

HRID 1612935 reaction equation
[Br:1][C@@H:2]([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[Br:1][C@@H:2]([CH2:5][CH2:6][O:7][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:3][O:4][S:16]([CH3:15])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11095044105601-94-3

Product 1

HCID 10892715HCID 10892715, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 70 g (0.414 mol) (S)-2-bromo -1,4-butanediol in 1.5 liters methylene chloride was cooled in ice and 173 ml (1.24 mol) triethylamine (dried over potassium hydroxide) was added to give a clear solution. To this was added dropwise over 80 minutes at 5° to 15° C., 96 ml (1.24 mol) methanesulfonyl chloride. The mixture was then stirred at room temperature for 2.5 hours, washed 2×750 ml with water and 1×750 ml brine, dried (MgSO4), and the solvent evaporated to give an amber oil which was purified by chromatography on a 140 mm×25 cm silica gel column, eluting with 9:1 chloroform:ethyl acetate. The product fractions were combined and solvent evaporated to give 105 g (97%) of the title compound as a waxy white solid; [alpha]D=- 34.49° (c=5 in CHCl3).

Workup

  1. customto give a clear solution
  2. additionTo this was added dropwise over 80 minutes at 5° to 15° C.
  3. washwashed 2×750 ml with water and 1×750 ml brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated
  6. customto give an amber oil which
  7. customwas purified by chromatography on a 140 mm×25 cm silica gel column
  8. washeluting with 9:1 chloroform
  9. customsolvent evaporated

Sources & evidence

ORD record
ord-2c08d24af0514de7a0e80e7101de17d1
Source dataset
uspto-grants-1993_03
Patent number
US05191077

Reaction notes

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