Triethylamine → 1-Methylsulfonyloxy-5-phenylpentane

HRID 1357010Notes

Reaction equation

HRID 1357010 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.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][S:14]([CH3:13])(=[O:16])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 615235-Phenyl-1-pentanol

Product 1

HCID 116301071-Methylsulfonyloxy-5-phenylpentaneYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Operating analogously to example 19 using 5-phenylpentanol (7.18 ml, 7 g, 42.6 mmoles) in methylene chloride (8 ml) and methyl-sulfonyl chloride (3.63 ml, 5.37 g, 46.9 mmoles) in methylene chloride (4 ml), and also using triethylamine (6.82 ml, 4.96 g, 49 mmoles) to adjust the pH after the addition of methyl-sulfonyl chloride, 10.57 g of the title product were obtained after half an hour of reaction (stoichiometric yield).

Sources & evidence

ORD record
ord-4f6983b8267547fe951cfe9a4186bf8c
Source dataset
uspto-grants-2003_07
Patent number
US06589951B1

Reaction notes

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