Dichloromethane → HCID 86737363, compound

HRID 1732271Notes

Reaction equation

HRID 1732271 reaction equation
[OH:1][CH2:2][CH:3]([CH3:20])[CH2:4][CH2:5][CH2:6][CH:7]1[CH:13]2[O:14][C:10]([CH2:15][C:16]([O:18][CH3:19])=[O:17])([CH2:11][CH2:12]2)[CH2:9][O:8]1.[CH2:21](Cl)Cl>>[CH3:21][C:7]1([CH2:6][CH2:5][CH2:4][CH:3]([CH3:20])[CH:2]=[O:1])[CH:13]2[O:14][C:10]([CH2:15][C:16]([O:18][CH3:19])=[O:17])([CH2:11][CH2:12]2)[CH2:9][O:8]1

Participants

3

Reactant 2

HCID 6344Dichloromethane2×HCID 86737364HCID 86737364, compound

Product 1

HCID 86737363HCID 86737363, compound

Procedure

A mixture of methyl (1RS,4SR,5RS)-4-(5-hydroxy-4-methyl-pentyl)-3,8-dioxabicyclo [3.2.1] octane-1-acetate (420 mg, 1.4 mM) and methylene chloride (5 ml) is added to a mixture of chromium trioxide-pyridine complex (10 mM), methylene chloride (20 ml) and Celite (2 g) at 0° C. and stirred for four hours under nitrogen. The resulting mixture is filtered and washed with ether (100 ml). The filtrate is treated with ether (200 ml) and washed with saturated sodium bicarbonate solution (3×100 ml), saturated cupric sulfate solution (2×100 ml) and dried (sodium sulfate). The solvent is removed in vacuo to give methyl (1RS,4SR,5RS)-4-methyl-4-(4-methyl-5-oxopentyl)-3,8-dioxabicyclo [3.2.1] octane-1-acetate as a colorless oil. This material is homogeneous by thin layer chromatography.

Workup

  1. filtrationThe resulting mixture is filtered
  2. washwashed with ether (100 ml)
  3. additionThe filtrate is treated with ether (200 ml)
  4. washwashed with saturated sodium bicarbonate solution (3×100 ml), saturated cupric sulfate solution (2×100 ml)
  5. dry with materialdried (sodium sulfate)
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2d4eba29e2e2488b945d6e23cea74976
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Reaction notes

Loading…