Dimethyl Carbonate → HCID 54535260, compound

HRID 1638819Notes

Reaction equation

HRID 1638819 reaction equation
[CH2:1]([O:8][C:9]1[C:20]([O:21][CH3:22])=[CH:19][C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[C:26](=O)([O:29]C)[O:27][CH3:28]>>[CH3:28][O:27][C:26]([CH:16]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:19]=[C:20]([O:21][CH3:22])[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[C:17]1=[O:18])=[O:29]

Participants

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 12478227HCID 12478227, compound

Product 1

HCID 54535260HCID 54535260, compound

Procedure

A mixture of 3-benzyloxy-2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (3.2 g), sodium methoxide (2.8 g) and dimethyl carbonate (100 ml) is heated for four hours under reflux in a stream of nitrogen. The reaction mixture is poured into ice-water containing concentrated hydrochloric acid (10 ml), and extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated under reduced pressure to afford 3-benzyloxy-2-methoxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid methyl ester (3.7 g) as a pale yellow oily product.

Workup

  1. temperatureis heated for four hours
  2. temperatureunder reflux in a stream of nitrogen
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-95118521a1204520a1df47ff149df232
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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