Water → HCID 21268679, compound

HRID 868626Notes

Reaction equation

HRID 868626 reaction equation
C[O:2][C:3]1[C:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:6]2[CH2:7][CH2:8][O:9][C:5]=2[C:4]=1[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.B(Cl)(Cl)Cl.O>ClCCl>[OH:2][C:3]1[C:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:6]2[CH2:7][CH2:8][O:9][C:5]=2[C:4]=1[C:18](=[O:27])[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 21287551HCID 21287551, compound

Product 1

HCID 21268679HCID 21268679, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 6-methoxy-7-(4-methoxybenzoyl)-2,3-dihydrobenzofuran-5-ylacetate (3.6 g) was dissolved in dichloromethane (40 ml) and cooled to 0° C. To this was added boron trichloride (30 ml 1M). The reaction was allowed to warm to room temperature and, after 2 hours, added to water. The dichloromethane solution was washed 2 times with water, dried, and evaporated. The residue was run on a silica gel column, being eluted with ethyl acetate/hexane to give ethyl 6-hydroxy-7-(4-methoxybenzoyl)-2,3-dihydrobenzofuran-5-ylacetate. Saponification as per Example 3 gave 6-hydroxy-7-(4-methoxybenzoyl)-2,3-dihydrobenzofuran-5-ylacetic acid.

Workup

  1. temperatureto warm to room temperature and, after 2 hours
  2. washThe dichloromethane solution was washed 2 times with water
  3. customdried
  4. customevaporated
  5. washbeing eluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-690b2e5db9534400b4d4079202431d4f
Source dataset
uspto-grants-1988_10
Patent number
US04780480

Reaction notes

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