Methanol → HCID 14579734, compound

HRID 1153920Notes

Reaction equation

HRID 1153920 reaction equation
[CH3:1][O-:2].[Na+].[Na].[OH:5][C:6]1[CH:7]=[C:8]([O:22][CH:23]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:24])[CH:9]=[C:10]2[C:15]=1[CH:14]([CH2:16][C:17]([OH:19])=[O:18])[CH2:13][C:12]([CH3:21])([CH3:20])[CH2:11]2.[CH3:34]O>>[C:1]([O:5][C:6]1[CH:7]=[C:8]([O:22][CH:23]([CH2:25][CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH3:24])[CH:9]=[C:10]2[C:15]=1[CH:14]([CH2:16][C:17]([OH:19])=[O:18])[CH2:13][C:12]([CH3:21])([CH3:20])[CH2:11]2)(=[O:2])[CH3:34]

Participants

5

Reactant 4

HCID 887MethanolHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 54085988HCID 54085988, compound

Product 1

HCID 14579734HCID 14579734, compoundYield 47%

Procedure

To a solution of sodium methoxide prepared from 0.2 g. sodium metal and 32 ml. methanol is added a solution of 0.20 g. (0.53 mmole) of the lactone of 2-[8-hydroxy-3,3-dimethyl-6-(5-phenyl-2-pentyloxy)tetralin-1-yl]acetic acid and the mixture is stirred for 30 minutes. The methanol is evaporated in vacuo, the residue is cooled in ice and a cold solution of 6.4 ml. acetyl chloride in 12.8 ml. ethyl acetate is added and the resulting mixture stirred 15 minutes. The mixture is concentrated to dryness in vacuo, the residue taken up in fresh ethyl acetate, washed with water, brine and dried (MgSO4) to yield 0.30 g. yellow oil. The oil is purified on a silica gel column using mixtures of methylene chloride and methanol as eluant to afford 110 mg. (47%) of title compound. 1H-NMR (CDCl3) ppm (delta): 0.8 (s, 3H), 1.03 (s, 3H), 1.23 (d, 4H), 1.7 (m, 6H), 2.3 (s, 3H), 2.5 (m, 4H), 2.9 (m, 1H), 3.13 (m, 1H), 4.2 (m, 1H), 6.4 (s, 2H), 7.13 (s, 5H).

Workup

  1. customThe methanol is evaporated in vacuo
  2. temperaturethe residue is cooled in ice
  3. additionethyl acetate is added
  4. concentrationThe mixture is concentrated to dryness in vacuo
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. customto yield 0.30 g
  8. customThe oil is purified on a silica gel column
  9. customto afford 110 mg

Sources & evidence

ORD record
ord-265749745c694839bc3434924bff08c4
Source dataset
uspto-grants-1984_12
Patent number
US04486428

Reaction notes

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