Water → HCID 66699641, compound

HRID 1818538Notes

Reaction equation

HRID 1818538 reaction equation
[OH:1][C:2]1[C:3]([CH3:36])=[C:4]([CH:29]=[CH:30][C:31]=1[C:32](=[O:35])[CH2:33][CH3:34])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#N)=[CH:9][CH:8]=1.[OH-:37].[K+].[OH2:39]>C(O)C>[OH:1][C:2]1[C:3]([CH3:36])=[C:4]([CH:29]=[CH:30][C:31]=1[C:32](=[O:35])[CH2:33][CH3:34])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]([OH:39])=[O:37])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57884484HCID 57884484, compound

Product 1

HCID 66699641HCID 66699641, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared essentially as described in Preparation 113 employing 3-[[4-(3-hydroxy-2-methyl-4-propionyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (5.00 g, 10.3 mmol) and potassium hydroxide (11.6 g, 206 mmol) in ethanol (100 mL) and water (25 mL) at reflux for 3 days. Concentrate the reaction mixture and acidify with 1N hydrochloric acid, then extract with dichloromethane (3×). Combine organic layers, dry (sodium sulfatesodium sulfate) and evaporate to afford the title compound as a white solid (2.11 g, 4.18 mmol, 40%): MS (m/z): 503 (M−H).

Workup

  1. customThe title compound is prepared essentially
  2. temperatureat reflux for 3 days
  3. concentrationConcentrate the reaction mixture
  4. extractionextract with dichloromethane (3×)
  5. dry with materialCombine organic layers, dry (sodium sulfatesodium sulfate)
  6. customevaporate

Sources & evidence

ORD record
ord-c4e52da2e3324f4fab0fb49fd34e8fb8
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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