Water → HCID 15448809, compound

HRID 275773Notes

Reaction equation

HRID 275773 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]2[C:21]([O:22]C=O)=[C:20]([O:25][CH2:26][C@@H:27]3[O:29][CH2:28]3)[CH:19]=[CH:18][C:10]=2[S:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].O>O1CCCC1>[Cl:7][C:8]1[C:9]2[C:21]3[O:22][C@@H:27]([CH2:28][OH:29])[CH2:26][O:25][C:20]=3[CH:19]=[CH:18][C:10]=2[S:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 15448807HCID 15448807, compound

Product 1

HCID 15448809HCID 15448809, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Saturated aqueous potassium carbonate solution (20 ml) was added to a stirred solution of ethyl (R)-3-chloro-5-(2,3-epoxypropoxy)-4-formyloxy-benzo[b]thiophene-2-carboxylate (1.85 g, prepared as described above) in tetrahydrofuran (20 ml) and the mixture stirred for 24 hours at room temperature. The reaction mixture was poured into water (200 ml) and extracted with ethyl acetate (2×100 ml). The combined extracts were dried over sodium sulphate and evaporated under reduced pressure to give a yellow solid. Purification by flash chromatography on silica using a 1:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate as eluant gave ethyl (S)-9-chloro-2,3-dihydro-2-(hydroxymethyl)thieno[3,2-f]-1,4-benzodioxin-8-carboxylate (1.44 g) as a pale-yellow solid; m.p. 165-166° C.

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined extracts were dried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customto give a yellow solid
  5. customPurification by flash chromatography on silica using
  6. additiona 1:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate as eluant

Sources & evidence

ORD record
ord-56d95630b3dd43c5b350bae49fcf9fef
Source dataset
uspto-grants-2002_03
Patent number
US06353002B2

Reaction notes

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