Acetic Acid → HCID 53694759, compound

HRID 1578668Notes

Reaction equation

HRID 1578668 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:11]1[CH:16]=[CH:17][CH:18]([O:26]C(=O)C)[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C[O-].[Na+].C(O)(=O)C>CO>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:11]1[CH:16]=[CH:17][CH:18]([OH:26])[CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 54340383HCID 54340383, compound

Product 1

HCID 53694759HCID 53694759, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of trans-2-(4-cyclohexyl-3-acetoxy-1-butenyl)-5-oxocyclopentaneheptanoic acid methyl ester (265 g), prepared as described in Example 9, in methanol (287 ml) is added a solution of sodium methoxide (prepared from 172 g of sodium and 148 ml of methanol). The reaction mixture is stirred at room temperature for 90 min. then rendered neutral with one equivalent of acetic acid. The solvent is evaporated. The residue is taken up in ether. The ether solution is washed with water, dried and the solvent removed to yield the title compound, νmaxCHCl3 3,450, 1,735 cm-1.

Workup

  1. customprepared
  2. customThe solvent is evaporated
  3. washThe ether solution is washed with water
  4. customdried
  5. customthe solvent removed

Sources & evidence

ORD record
ord-8d5725cd254d4041b4e8105a7d558837
Source dataset
uspto-grants-1976_02
Patent number
US03937801

Reaction notes

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