Water → 1-Methylsulfonyloxy-5-phenylpentane

HRID 378973Notes

Reaction equation

HRID 378973 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][S:21]([CH3:20])(=[O:23])=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 615235-Phenyl-1-pentanol

Product 1

HCID 116301071-Methylsulfonyloxy-5-phenylpentaneYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Phenyl-pentanol (40 g, 244 mmoles) in methylene chloride (80 ml) at 0° C. was added with triethylamine (39 ml, 28.34 g, 280 mmoles) and a solution of methyl-sulfonyl chloride (20.7 ml, 30.69 g, 268 mmoles) in methylene chloride (40 ml). The temperature was left to rise to the room value, then the mixture was poured into water and the organic phase was isolated, washed with water, anhydrified and concentrated to give 59.49 g of the title product (yield: 99%).

Workup

  1. waitThe temperature was left
  2. customthe organic phase was isolated
  3. washwashed with water, anhydrified
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-23c3cb3c1e2c4f0389ecf98416913ab2
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

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