Sodium Hydroxide → HCID 21272033, compound

HRID 1193482Notes

Reaction equation

HRID 1193482 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[C:9]2[C:5]([C:6]3[CH2:20][CH2:19][O:18][C:17]([CH2:26][CH3:27])([CH2:21][C:22]([O:24]C)=[O:23])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:10]([O:11][CH2:12][C:13]([F:14])([F:15])[F:16])=[C:9]2[C:5]([C:6]3[CH2:20][CH2:19][O:18][C:17]([CH2:26][CH3:27])([CH2:21][C:22]([OH:24])=[O:23])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21272045HCID 21272045, compound

Product 1

HCID 21272033HCID 21272033, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 7-chloro-1-ethyl-1,3,4,9-tetrahydro-8-(2,2,2-trifluoroethoxy)-pyrano[3,4-b]indole-1-acetate (3.2 g, 8 mmol) EtOH (25 mL) and 1N NaOH (10 mL) was refluxed for 2 hours. At the end of this time the EtOH was removed in vacuo and the rsidue diluted with H2O (25 mL). This aqueous mixture was acidified with 1N HCl, then extracted with ether (150 mL). The ether layer was washed with saturated brine (2×100 mL), dried (MgSO4), and concentrated to yield a light yellow oil. This oil was dissolved in toluene and petroleum ether added (~10 volumes). After cooling, the crystals were removed by filtration to yield 2.8 g (90%) of 7-chloro-1-ethyl-1,3,4,9-tetrahydro-8-(2,2,2-trifluoroethoxy)-pyrano[3,4-b]indole-1-acetic acid, m.p. 157° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAt the end of this time the EtOH was removed in vacuo
  3. additionthe rsidue diluted with H2O (25 mL)
  4. extractionextracted with ether (150 mL)
  5. washThe ether layer was washed with saturated brine (2×100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto yield a light yellow oil
  9. temperatureAfter cooling
  10. customthe crystals were removed by filtration

Sources & evidence

ORD record
ord-c65c44088a7844418e28df6c5029f475
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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