Pivaloyl chloride → HCID 546152, compound

HRID 1586904Notes

Reaction equation

HRID 1586904 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH:8][CH2:9][C@H:10]1[CH2:15][CH:14]=[CH:13][CH2:12][C@H:11]1[OH:16]>N1C=CC=CC=1.CO.CCOCC>[C:1]([O:8][CH2:9][CH:10]1[CH2:15][CH:14]=[CH:13][CH2:12][CH:11]1[OH:16])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 62493Pivaloyl chlorideHCID 14827124HCID 14827124, compound

Product 1

HCID 546152HCID 546152, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Pivaloyl chloride (1.036 g, 1.1 equivalents) was added at -20° C. to a solution of 2-hydroxymethyl-cyclohex-4-eneol (7, 1.00 g, 7.81 mmol) in pyridine (10 ml). The reaction mixture was kept at -20° C. for 20 hours, diluted with methanol and ether (50 ml), and the organic layer extracted with 20 ml portions of 10% HCl containing copper sulfate until the blue color in the organic layer had disappeared. The ethereal layer was dried (magnesium sulfate), the solvent removed under vacuum, and the residue chromatographed on silica gel (hexane:EtOAc 7:3, Rf=0.43) to yield 2-pivaloyloxymethyl-cyclohex-4-eneol (8, 1.54 g, 93%) as a colorless oil. (IR, CCl4 1730 cm-1). 3,4-trans 1-Methoxy-3-pivaloyloxymethyl-4-(2'-hydroxyethyl)-tetrahydrofuran 9 and 1-Methoxy-3-pivaloyloxymethyl-4-(2',2'-dimethoxyethyl)-tetrahydrofuran.

Workup

  1. extractionthe organic layer extracted with 20 ml portions of 10% HCl
  2. additioncontaining copper sulfate until the blue color in the organic layer
  3. dry with materialThe ethereal layer was dried (magnesium sulfate)
  4. customthe solvent removed under vacuum
  5. customthe residue chromatographed on silica gel (hexane:EtOAc 7:3, Rf=0.43)

Sources & evidence

ORD record
ord-d7e7270ddb9b4378ae50729a80f1914c
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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