Methanol → HCID 19885950, compound

HRID 654923Notes

Reaction equation

HRID 654923 reaction equation
[OH:1][CH:2]([C:15]1[CH:19]([OH:20])[O:18][C:17](=[O:21])[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:22]O>B(F)(F)F.CCOCC.C(Cl)Cl>[OH:1][CH:2]([C:15]1[CH:19]([O:20][CH3:22])[O:18][C:17](=[O:21])[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 887MethanolHCID 15037057HCID 15037057, compound

Product 1

HCID 19885950HCID 19885950, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.8 g. of 4-(1-hydroxytridecyl)-5-hydroxy-2(5H)-furanone and 43 ml of methanol with a catalytic amount of BF3.OEt2 (3 drops) is stirred under argon for 15 hours. The mixture is diluted with methylene chloride, washed with water and dried over magnesium sulfate. The mixture is filtered and the solvent removed in vacuo. The resulting oil is purified by flash chromatography to give 4-(1-hydroxytridecyl)-5-methoxy-2(5H)-furanone.

Workup

  1. additionA mixture of 0.8 g
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe mixture is filtered
  5. customthe solvent removed in vacuo
  6. customThe resulting oil is purified by flash chromatography

Sources & evidence

ORD record
ord-16afd647c6704e1fa274f1035fb49050
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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