Sodium Hydroxide → HCID 53936787, compound

HRID 1637109Notes

Reaction equation

HRID 1637109 reaction equation
[C:1]1([C:7]#[C:8][CH:9]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:19]=2)[CH2:10][C:11](=[O:17])[CH2:12][O:13]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O>[C:1]1([C:7]#[C:8][CH:9]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:19]=2)[CH2:10][C:11](=[O:17])[CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54564316HCID 54564316, compound

Product 1

HCID 53936787HCID 53936787, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (+/-)-1-phenyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-oxo-6-acetoxyhexyne (130 mg, 0.34 mmol) in MeOH (2 ml) was treated with NaOH (0.1 ml of a 2.5N solution), and the mixture was stirred at 23° for 3.5 hr. The reaction was diluted with H2O, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent removed. Purification by flash chromatography (silica gel, 50% Et2O in CH2Cl2) gave the titled compound as an oil (32 mg, 28%). 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.32 (m, 3 H), 6.98 (m, 2 H), 6.86 (d, 1 H), 4.80 (m, 1 H), 4.38 (t, 1 H), 4.32 (d, 1 H), 4.14 (d, 1 H), 3.84 (s, 3 H), 3.00 (d of d, 1 H), 2.86 (d of d, 1 H), 1.68-2.00 (m, 6 H), 1.62 (m, 2 H).

Workup

  1. extractionextracted with Et2O
  2. washThe extracts were washed with H2O
  3. customdried
  4. customthe solvent removed
  5. customPurification by flash chromatography (silica gel, 50% Et2O in CH2Cl2)

Sources & evidence

ORD record
ord-7c29948d9e0d417a9a96324863125bff
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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