Sodium Hydroxide → HCID 86628704, compound

HRID 2422928Notes

Reaction equation

HRID 2422928 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C:12]([O:14]CC)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:8])=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86628703HCID 86628703, compound

Product 1

HCID 86628704HCID 86628704, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ester 16 (1.05 g, 3.281 mmol) in ethanol (4 ml) was treated at room temperature with 5% NaOH aqueous solution (2.6 ml). The resulting mixture was stirred at room temperature for 3 h. The ethanol was removed in vacuo and aqueous 5% HCl solution (2.6 ml) was added. The aqueous mixture was extracted with chloroform and the organic extracts dried (Na2SO4), filtered and the solvent removed under reduced pressure. The remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (806 mg, 84%). δH (400 MHz, MeOD) 4.66 (2H, s, CH2), 7.41-7.51 (3H, m, ArH), 7.69 (2H, d, J=7.2 Hz, ArH), 7.87 (2H, d, J=8.4 Hz, ArH), 8.01 (2H, d, J=8.4 Hz, ArH); δc (100.6 MHz, MeOD) 64.9, 127.2, 127.7, 128.6, 128.7, 129.0, 134.5, 139.1, 147.2, 168.2.

Workup

  1. customThe ethanol was removed in vacuo and aqueous 5% HCl solution (2.6 ml)
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with chloroform
  4. dry with materialthe organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (806 mg, 84%)

Sources & evidence

ORD record
ord-2de44f961a3a4c0687915478d2201626
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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