Trimethyl orthoformate → HCID 70596593, compound

HRID 1706860Notes

Reaction equation

HRID 1706860 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH:15]=[CH:16][C:17]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12]C1=O.CO[CH:31]([O:34][CH3:35])[O:32][CH3:33]>>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH:15]=[CH:16][C:17]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][C:31]1([O:32][CH3:33])[O:34][CH3:35]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 70596212HCID 70596212, compound

Product 1

HCID 70596593HCID 70596593, compound

Procedure

A mixture of 1.5 g of 9-oxo-15,15-ethylenedioxy-13-prostenoic acid methyl ester, 20 ml of trimethoxy-methane and 3 drops of concentrated H2SO3 is boiled for 6 hours. 15 ml of the solvent is distilled within 2 hours. The residue is diluted with 30 ml of diethyl ether, washed with aqueous saturated NaHCO3 solution and H2O and dried over MgSO4. The solvent is distilled. After chromatographic purification of the residue (silica gel/diisopropyl ether), 9,9-dimethoxy-15,15-ethylenedioxy-13-prostenoic acid methyl ester is obtained.

Workup

  1. distillation15 ml of the solvent is distilled within 2 hours
  2. additionThe residue is diluted with 30 ml of diethyl ether
  3. washwashed with aqueous saturated NaHCO3 solution and H2O
  4. dry with materialdried over MgSO4
  5. distillationThe solvent is distilled
  6. customAfter chromatographic purification of the residue (silica gel/diisopropyl ether)

Sources & evidence

ORD record
ord-de23b66584d948899be9930636edbcb1
Source dataset
uspto-grants-1980_06
Patent number
US04209444

Reaction notes

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