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

HRID 1375277

Reaction equation

HRID 1375277 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-1592d15cc0244fdea89d2984c00303e9
Source dataset
uspto-grants-2007_01
Patent number
US07166726B2

Linked notes

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