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

HRID 590996ノート

反応式

HRID 590996 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-36240e869e3c4133a173d5fe7ac623b4
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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