Lithium Hydroxide → 4-[2,2-Dimethyl-4-(5-methyl-thiophen-2-yl)-2H-benzo[g]chromen-7-yl]-benzoic acid

HRID 2622

Reaction equation

HRID 2622 reaction equation
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[CH:23]=[C:22]4[C:17]([C:18]([C:26]5[S:27][C:28]([CH3:31])=[CH:29][CH:30]=5)=[CH:19][C:20]([CH3:25])([CH3:24])[O:21]4)=[CH:16][C:15]=3[CH:32]=2)=[CH:7][CH:6]=1)C.[Li+].[OH-]>CO.C1COCC1.O>[CH3:24][C:20]1([CH3:25])[CH:19]=[C:18]([C:26]2[S:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[C:17]2[C:22](=[CH:23][C:14]3[CH:13]=[CH:12][C:11]([C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:33])=[O:3])=[CH:6][CH:7]=4)=[CH:32][C:15]=3[CH:16]=2)[O:21]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 15887284Ethyl4-[2,2-dimethyl-4-(5-methyl-thien-2-yl)-benzo[1,2-g]-chrom-3-en-7-yl]benzoate2×

Product 1

HCID 98453824-[2,2-Dimethyl-4-(5-methyl-thiophen-2-yl)-2H-benzo[g]chromen-7-yl]-benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-4-[2,2-dimethyl-4-(5-methyl-thien-2-yl)-benzo[1,2-g]-chrom-3-en-7-yl]benzoate (Compound 11, 18 mg, 0.03 mmol) in methanol (0.5 mL) and THF (1 mL), was added LiOH in water (1M solution, 0.3 mL). The reaction mixture was stirred for 20 hours, the solvent was removed under reduced pressure, the residue dissolved in water (5 mL), washed with ether (10 mL) and the aqueous layer was acidified to PH 5. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried, and the solvent was removed under reduced pressure to afford the title compound as a pale yellow solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in water (5 mL)
  3. washwashed with ether (10 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6f1adbd425794bcdbe2ae73da2aa8582
Source dataset
uspto-grants-1998_03
Patent number
US05728846

Linked notes

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