Potassium Hydroxide → HCID 18973695, compound

HRID 2399432Notes

Reaction equation

HRID 2399432 reaction equation
[C:1]([C:5]1[CH2:10][C:9]([C:24]#[N:25])([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:12]=2)[CH2:8][CH2:7][C:6]=1[O:26][CH2:27][O:28][CH3:29])([O:3]C)=[O:2].[OH-].[K+]>CO.O1CCCC1.O>[C:1]([C:5]1[CH2:10][C:9]([C:24]#[N:25])([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH:12]=2)[CH2:8][CH2:7][C:6]=1[O:26][CH2:27][O:28][CH3:29])([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 18973699HCID 18973699, compound

Product 1

HCID 18973695HCID 18973695, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-carbomethoxy-4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)-1-(methoxymethyloxy)cyclohex-1-ene (0.5 g, 1.25 mmol) and potassium hydroxide (0.21 g, 3.75 mmol) in methanol (13 mL), tetrahydrofuran (5 mL) and water (7.5 mL) under an argon atmosphere was heated at 65° C. for 3 h. The mixture was partitioned between methylene chloride and acidic water, was extracted twice, the organic layer was dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 5% methanol/chloroform, provided an oil (0.26 g, 54%).

Workup

  1. customThe mixture was partitioned between methylene chloride and acidic water
  2. extractionwas extracted twice
  3. dry with materialthe organic layer was dried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customPurification by flash chromatography
  6. washeluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-8103d7329f0c43238dadd2581e9d16c7
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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