Sodium Hydroxide → HCID 18790061, compound

HRID 1107156Notes

Reaction equation

HRID 1107156 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]2[C:14]3([CH2:18][CH2:17][CH2:16][CH2:15]3)[C:13](=[O:19])[O:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([SH:30])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].[OH-].[Na+]>C(O)(C)C>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:30][CH:11]([C:14]2([C:13]([OH:12])=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1365393,4-Dimethoxybenzene-1-thiolHCID 18790109HCID 18790109, compound

Product 1

HCID 18790061HCID 18790061, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-Phenylbutyl)-2-oxaspiro[3,4]octan-1-one (2 g, 7.7 mmol) and 3,4-dimethoxybenzenethiol (2 g, 11.7 mmol) are dissolved in isopropanol (30 mL) and cooled to 0° C. A 1 M solution of NaOH (9.7 mL, 9.7 mmol) is added slowly, and after 5 minutes at 0° C., the reaction is allowed to stir at room temperature overnight. The solvent is removed in vacuo and the residue is dissolved in CH2Cl2 (100 mL). This solution is washed with 1 N HCl (50 mL), brine (30 mL) and dried over MgSO4. The solution is concentrated in vacuo and the crude product is purified by column chromatography (silica, 1% MeOH in CH2Cl2) to yield 1-[1-(3,4-dimethoxyphenylsulfanyl)-5-phenylpentyl]-cyclopentanecarboxylic acid (2.2 g, 65%). 1H NMR (300 MHz, CDCl3) δ 7.28-7.23 (m, 2H), 7.18-7.09 (m, 3H), 7.01-6.91 (m, 2H), 6.76 (d, J=8.1 Hz, 1H), 3.86 (s, 3H), 3.84 (s, 3H), 3.31 (dd, J=10.0, 3.0 Hz, 1H), 2.58-2.51 (m, 2H), 2.18-2.08 (m, 2H), 1.89-1.40 (m, 12H); MS (EI) m/e 428 (M+).

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in CH2Cl2 (100 mL)
  3. washThis solution is washed with 1 N HCl (50 mL), brine (30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationThe solution is concentrated in vacuo
  6. customthe crude product is purified by column chromatography (silica, 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-72917f78e1dd4836924d04445e3e93bd
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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