Pivaloyl chloride → HCID 19760159, compound

HRID 1586906Notes

Reaction equation

HRID 1586906 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:8]([O:15][CH2:16][CH2:17][CH:18]([OH:22])[CH2:19][CH2:20][OH:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)=O.CC(C)=O>N1C=CC=CC=1.CO.C(Cl)Cl>[C:1]([O:21][CH2:20][CH2:19][CH:18]([OH:22])[CH2:17][CH2:16][O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 62493Pivaloyl chlorideHCID 18522661Acetone cardiceHCID 197601555-Benzyloxy-1,3-pentanediol

Product 1

HCID 19760159HCID 19760159, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Pivaloyl chloride (2.070 ml, 17.1 mmol) was added slowly to a solution of 5-benzyloxy-1,3-pentanediol (39, 16.3 mmol) in anhydrous pyridine (35 ml) at -18° C. (dry ice-acetone bath). The mixture was kept without stirring in a -20° freezer for 15 hours. The reaction mixture was then diluted with methanol (1 ml) and CH2Cl2 (50 ml), and extracted with 10% HCl containing copper sulfate (10 g/l) until the blue color in the organic layer was removed. The aqueous layer was re-extracted with methylene chloride, the combined organic layers are dried (magnesium sulfate), the solvent evaporated, and 1-pivaloyloxy-5-benzyloxy-3-pentanol (40) isolated as a colorless oil by flash chromatography on silica gel (hexane/EtOAc 7:3 as eluant; yield 4.05 g, 86% as a colorless oil).

Workup

  1. extractionextracted with 10% HCl
  2. additioncontaining copper sulfate (10 g/l) until the blue color in the organic layer
  3. customwas removed
  4. extractionThe aqueous layer was re-extracted with methylene chloride
  5. dry with materialthe combined organic layers are dried (magnesium sulfate)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-143c3ca8e13b4c198395c93e787f99c1
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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