Lithium hydroxide, monohydrate → HCID 10187249, compound

HRID 1835609Notes

Reaction equation

HRID 1835609 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[C:23]([OH:25])[C:22]([C:26](=[O:28])[CH3:27])=[CH:21][C:20]=2[CH2:29][CH3:30])=[CH:10][CH:9]=[CH:8][C:7]=1[O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39]C)=[O:38].O.[OH-].[Li+]>O1CCCC1.O>[C:37]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][O:31][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[C:23]([OH:25])[C:22]([C:26](=[O:28])[CH3:27])=[CH:21][C:20]=2[CH2:29][CH3:30])[C:6]=1[CH2:5][CH2:4][C:3]([OH:41])=[O:2])([OH:39])=[O:38]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22089203HCID 22089203, compound

Product 1

HCID 10187249HCID 10187249, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(6-Methoxy-6-oxohexyloxy)-6-[6-[[4-acetyl-2-ethyl-5-hydroxyphenyl]oxy]hexyl]benzenepropanoic acid methyl ester (25.8 mg, 0.0452 mmol) was dissolved in tetrahydrofuran (5 mL). Lithium hydroxide monohydrate (18.9 mg, 0.452 mmol) was dissolved in water (1 mL) and added to the reaction. The reaction was stirred for 18 h. The reaction was then concentrated, brought up in water, acidified to pH 5 with 1N HCl, and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered, and evaporated. The resulting oil recrystallized with hexane:ethyl acetate to give 24.5 mg (100%) of product. MS: Calcd. For C31H42O8+H, 543.2958; Found, 543.2946

Workup

  1. additionadded to the reaction
  2. concentrationThe reaction was then concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting oil recrystallized with hexane

Sources & evidence

ORD record
ord-de3e0c3a3605439d91d359b1cbc40f87
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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