Sodium Hydroxide → 1-(2-Chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanone

HRID 916048Notes

Reaction equation

HRID 916048 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[CH:26][C:25]=1[CH2:32][CH:33]([OH:47])[CH2:34][C:35]([C:38]1[C:46]2[O:45][CH2:44][CH2:43][C:42]=2[CH:41]=[CH:40][CH:39]=1)([CH3:37])[CH3:36].[OH-].[Na+]>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[CH:26][C:25]=1[CH2:32][C:33](=[O:47])[CH2:34][C:35]([C:38]1[C:46]2[O:45][CH2:44][CH2:43][C:42]=2[CH:41]=[CH:40][CH:39]=1)([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 589600171-(2-Chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanol

Product 1

HCID 589599661-(2-Chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanoneYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Dess-Martin periodinane (661 mg) in CH2Cl2 (5 mL) was added 1-(2-chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanol (460 mg) in CH2Cl2 (1 mL) at 0° C. The mixture was warmed to room temperature and stirred for 1 hour. NaOH (1 M, 10 mL) was added. The organic phase was separated and the aqueous layer was extracted with 30 mL of CH2Cl2. The combined organic phases were dried over magnesium sulfate. The solvent was removed to yield 405 mg of 1-(2-chloro-4-cyanophenyl)-4-(2,3-dihydrobenzofur-7-yl)-4-methyl-2-pentanone as a yellow solid.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with 30 mL of CH2Cl2
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-33a0e477d7234b90a8ba6bb870c24416
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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