Potassium Hydroxide → 2-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-5-phenylthiophen-3-yl]acetic acid

HRID 590996Notes

Reaction equation

HRID 590996 reaction equation
[C:1]([O:5][CH:6]([C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:13][C:12]=1[C:22]1[CH:23]=[CH:24][C:25]2[O:30][CH2:29][CH2:28][CH2:27][C:26]=2[CH:31]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([O:5][CH:6]([C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:13][C:12]=1[C:22]1[CH:23]=[CH:24][C:25]2[O:30][CH2:29][CH2:28][CH2:27][C:26]=2[CH:31]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 70855249methyl 2-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-5-phenylthiophen-3-yl]acetate

Product 1

HCID 708189582-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-5-phenylthiophen-3-yl]acetic acidYield 84.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 2-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-5-phenylthiophen-3-yl]acetate (11j) (57 mg, 0.13 mmol) and potassium hydroxide (64 mg, 0.52 mmol) in a mixture of ethanol (2 mL) and water (6 mL) was refluxed for 4 hours. The mixture was concentrated in vacuo. Water (5 mL) was added and the aqueous layer was washed with diethyl ether (5 mL), then extracted with dichloromethane (5 mL). The organic layer was washed with 1N hydrochloric acid (5 mL), dried over sodium sulfate and evaporated to dryness to provide the desired acid (45 mg, 0.11 mmol, 81%) as a white solid.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionWater (5 mL) was added
  4. washthe aqueous layer was washed with diethyl ether (5 mL)
  5. extractionextracted with dichloromethane (5 mL)
  6. washThe organic layer was washed with 1N hydrochloric acid (5 mL)
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-36240e869e3c4133a173d5fe7ac623b4
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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