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

HRID 590996노트

반응식

HRID 590996 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-36240e869e3c4133a173d5fe7ac623b4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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