Methanol → HCID 70197011, compound

HRID 342453Notes

Reaction equation

HRID 342453 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:5]=1[C:6]([NH:8][C:9]1[C:14]2[O:15][C:16]([CH3:23])=[C:17]([C:18](OCC)=[O:19])[C:13]=2[C:12](CO)=[CH:11][CH:10]=1)=[O:7].[OH2:31].[CH3:32]O>>[Cl:3][C:4]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:5]=1[C:6]([NH:8][C:9]1[C:14]2[O:15][C:16]([CH3:23])=[C:17]([CH:18]([OH:19])[CH2:32][OH:31])[C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:7]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 70201155HCID 70201155, compound

Product 1

HCID 70197011HCID 70197011, compound

Procedure

Sodium borohydride (7 mg) was added to a solution of 7-(2,6-dichlorobenzoylamino)-3-(1-ethoxycarbonyl)hydroxymethyl-2-methylbenzo[b]furan (76 mg) in methanol (3 ml) at 4° C. The mixture was stirred at ambient temperature for 3 hours and poured into cold water. The separated oil was extracted with ethyl acetate and the extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by colum chromatography on silica gel and the obtained oil was crystallized from diethyl ether to give 7-(2,6-dichlorobenzoylamino)-3-(1,2-dihydroxyethyl)-2-methylbenzo[b]furan (35 mg).

Workup

  1. extractionThe separated oil was extracted with ethyl acetate
  2. washthe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by colum chromatography on silica gel
  6. customthe obtained oil was crystallized from diethyl ether

Sources & evidence

ORD record
ord-cd4288f78b1f4a93b8cd51e33b5a1e9e
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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