Sodium Hydroxide → HCID 86729585, compound

HRID 574236Notes

Reaction equation

HRID 574236 reaction equation
[CH2:1]([O:8][C:9]([CH3:24])([C:20]([F:23])([F:22])[F:21])[C:10]([O:12]CC1C=CC=CC=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([CH3:24])([C:20]([F:21])([F:22])[F:23])[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86729607HCID 86729607, compound

Product 1

HCID 86729585HCID 86729585, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 2-(benzyloxy)-3,3,3-trifluoro-2-methylpropanoate (Int. D3)(170 mg, 0.502 mmol) in MeOH (5 ml) was treated with 2M sodium hydroxide (0.502 ml, 1.005 mmol) 2M and stirred at RT for 2 h. The methanol was removed in vacuo and the residue was dissolved in water and washed with EtOAc. The aqueous phase acidified with 5M HCl and extracted with EtOAc. The combined organic extracts were washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo afford the title product as a clear; 1H NMR (400 MHz, DMSO-d6) δ 14.08 (1H, br s), 7.35 (5H, m), 4.62 (2H, dd), 1.64 (3H, s).

Workup

  1. customThe methanol was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f846809f007d43c496dd3a937108de3d
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

Loading…