Potassium Hydroxide → HCID 67603239, compound

HRID 1604464Notes

Reaction equation

HRID 1604464 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][C:13]([O:32][CH3:33])=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[K+]>CS(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][C:13]([O:32][CH3:33])=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69931180HCID 69931180, compound

Product 1

HCID 67603239HCID 67603239, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (±)-cis-3-(4-fluorophenyl)-7-methoxy-4-(4-(2-pyrrolidinoethoxy)phenyl)-chromane (1.0 g, 2.23 mmol) and powdered potassium hydroxide (0.25 g, 4.46 mmol) in dry DMSO (5 ml) was heated to 80° C. for 3 h. The mixture was diluted with water (100 ml) and the products extracted into ethyl acetate (3×100 ml). The combined extracts were washed with water, brine, dried over magnesium sulfate, and evaporated to give the crude multi-component product mixture as an orange gum. The title compound was partially purified by means of column chromatography on silica gel 60, with 5% methanol in dichloromethane as eluent. On evaporation the title compound was isolated as a mixture of the title compound with some of the unreacted cis-isomeric starting material. The title compound was fully purified by means of preparative HPLC: column: YMC 120 Å, 15 μm, 250×10 mm; eluent: 60% methanol in 50 mM aqueous ammonium acetate; flow: 10 ml/min; UV detection at 220 nm. Evaporation of the appropriate fractions gave the title compound as a colourless wax.

Workup

  1. extractionthe products extracted into ethyl acetate (3×100 ml)
  2. washThe combined extracts were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give the crude multi-component product mixture as an orange gum
  6. customThe title compound was partially purified by means of column chromatography on silica gel 60, with 5% methanol in dichloromethane as eluent
  7. customOn evaporation the title compound

Sources & evidence

ORD record
ord-93a01d3171924336bf140bcbfd219a2c
Source dataset
uspto-grants-1999_11
Patent number
US05994390

Reaction notes

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