Methanol → (1RS,4SR,5RS)-4-(3-methanesulfonyloxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octane

HRID 2058135Notes

Reaction equation

HRID 2058135 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][C:10]1([CH3:20])[CH:16]2[O:17][C:13]([CH:18]=[CH2:19])([CH2:14][CH2:15]2)[CH2:12][O:11]1.CO>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][C:10]1([CH3:20])[CH:16]2[O:17][C:13]([CH:18]=[CH2:19])([CH2:14][CH2:15]2)[CH2:12][O:11]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 31297Methanesulfonyl chlorideHCID 23349562(1RS,4SR,5RS)-4-(3-hydroxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octane

Product 1

HCID 23349567(1RS,4SR,5RS)-4-(3-methanesulfonyloxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octaneYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methanesulfonyl chloride (200 mg, 2.6 mM) is added slowly to a mixture of (1RS,4SR,5RS)-4-(3-hydroxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octane (333 mg, 1.6 mM) in methylene chloride (30 ml) and triethylamine (2 ml) at 0° C. and stirred for five minutes. The resulting mixture is treated with methanol (1 ml) and most of the solvent is removed in vacuo. The residue is filtered through a silica gel (20 g) column and washed with ether-petroleum ether (1:1, 300 ml). The solvent is removed in vacuo to give (1RS,4SR,5RS)-4-(3-methanesulfonyloxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octane (408 mg, 90%) as a colorless oil.

Workup

  1. customis removed in vacuo
  2. filtrationThe residue is filtered through a silica gel (20 g) column
  3. washwashed with ether-petroleum ether (1:1, 300 ml)
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6a624483a94f42229f6e25c89acec3d3
Source dataset
uspto-grants-1980_07
Patent number
US04215048

Reaction notes

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