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Water → 4-Cyano-4-(2-isopropyl-7-methoxybenzoxazol-4-yl)cyclohexanone

HRID 842602
Notes
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Reaction equation

HRID 842602 reaction equation
[C:1]([C:3]1([C:14]2[C:19]3[N:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[O:22][C:18]=3[C:17]([O:26][CH3:27])=[CH:16][CH:15]=2)[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].[Na+].[Cl-].O>CS(C)=O>[C:1]([C:3]1([C:14]2[C:19]3[N:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[O:22][C:18]=3[C:17]([O:26][CH3:27])=[CH:16][CH:15]=2)[CH2:8][CH2:7][C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 22614794Methyl 5-cyano-5-(2-isopropyl-7-methoxybenzoxazol-4-yl)-2-oxocyclohexanecarboxylate2×

Product 1

HCID 97967974-Cyano-4-(2-isopropyl-7-methoxybenzoxazol-4-yl)cyclohexanoneYield 77.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl Sulfoxide
Solvent

Conditions

Temperature
140 °C

Procedure

0.69 g (1.86 mmol) of methyl 5-cyano-5-(2-isopropyl-7-methoxybenzoxazol-4-yl)-2-oxocyclohexanecarboxylate (starting compound A8) is dissolved in 16 ml of DMSO, a solution of 0.73 g of NaCl in 2 ml of dist. water is added and the mixture is stirred at 140° C. for 8.5 h. After cooling the reaction mixture, it is diluted with 80 ml of dist. water and extracted with ethyl acetate, and the organic phase is separated off, dried over magnesium sulfate and concentrated to dryness in vacuo. After chromatography, the title compound (0.45 g) is obtained as a colorless solid. TLC, silica gel (glass plates), petroleum ether/ethyl acetate (7:3), Rf=0.56, m.p. 118° C.

Workup

  1. temperatureAfter cooling the reaction mixture, it
  2. additionis diluted with 80 ml of dist
  3. extractionwater and extracted with ethyl acetate
  4. customthe organic phase is separated off
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-bfd69fbee8c64b78bb92bf7726c308e3
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06376485B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes