Water → HCID 11076723, compound

HRID 1871938Notes

Reaction equation

HRID 1871938 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]1[CH2:28][C@@H:8]1[CH2:9][O:10][C:11]1[C:12]([O:25]C=O)=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]2.O>O1CCCC1>[OH:7][CH2:28][C@@H:8]1[O:25][C:12]2=[C:13]3[C:17](=[CH:18][CH:19]=[C:11]2[O:10][CH2:9]1)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]3

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 10902815HCID 10902815, compound

Product 1

HCID 11076723HCID 11076723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Saturated aqueous potassium carbonate solution (200 ml) was added to a stirred solution of ethyl (R)-5-(2,3-epoxypropoxy)-4-formyloxyindole-2-carboxylate (22.0 g; prepared in a similar manner to that described above) in tetrahydrofuran (250 ml) and the mixture was stirred at room temperature for 72 hours. The mixture was poured into water (1000 ml) and extracted with ethyl acetate (4×400 ml). The combined extracts were dried over sodium sulphate and the solvent evaporated under reduced pressure to give ethyl (S)-2,3-dihydro-2-(hydroxymethyl)-7H-1,4-dioxino[2,3-e]indole-8-carboxylate (17.65 g) as a pale purple solid; m.p. 152-153° C.

Workup

  1. customprepared in a similar manner to that
  2. extractionextracted with ethyl acetate (4×400 ml)
  3. dry with materialThe combined extracts were dried over sodium sulphate
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-72541328ec844dc6842586f1c35a3f3c
Source dataset
uspto-grants-2000_08
Patent number
US06107310

Reaction notes

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