Sodium Hydroxide → 3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butan-1-ol

HRID 844587Notes

Reaction equation

HRID 844587 reaction equation
C1C2C=CC=C(C([O:13][CH2:14][CH2:15][C@@H:16]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=3)[CH2:17][N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[C:23]([C:25]3[C:26]4[CH2:27][CH2:28][CH2:29][CH2:30][C:31]=4[CH:32]=[CH:33][CH:34]=3)=[O:24])=O)C=2CCC1.[OH-].[Na+]>CO>[Cl:42][C:37]1[CH:36]=[C:35]([C@@H:16]([CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[C:19]2[C:23]([C:25]2[C:26]3[CH2:27][CH2:28][CH2:29][CH2:30][C:31]=3[CH:32]=[CH:33][CH:34]=2)=[O:24])[CH2:15][CH2:14][OH:13])[CH:40]=[CH:39][C:38]=1[Cl:41]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 598865763(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butyl 1,2,3,4-tetrahydro-5-naphthoate

Product 1

HCID 540642943(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butan-1-olYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3(S)-(3,4-Dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butyl 1,2,3,4-tetrahydro-5-naphthoate (1.38 g) (see Preparation 101) was dissolved in methanol (40 ml), 1N aqueous sodium hydroxide solution (5 ml) added and the resulting mixture stirred at room temperature overnight. The methanol was then removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was separated, washed sequentially with saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give 3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butan-1-ol (0.82 g) as a gum.

Workup

  1. customThe methanol was then removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed sequentially with saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-80cae09519234c11a95ed5611d7fe4f9
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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