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Water → methyl 2-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-benzothiophen-3-yl]acetate

HRID 590965
ノート
印刷プレビュー

反応式

HRID 590965 の反応式
Br[C:2]1[S:3][C:4]2[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=2[C:6]=1[CH:7]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[Na+].[Na+].O.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[O:42][CH2:41][CH2:40][CH2:39]3)O1>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:13]([O:12][CH:7]([C:6]1[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[S:3][C:2]=1[C:36]1[CH:45]=[CH:44][C:43]2[O:42][CH2:41][CH2:40][CH2:39][C:38]=2[CH:37]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:16])([CH3:15])[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962Water2 回HCID 10340Sodium CarbonateHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70813729Methyl 2-(2-bromo-1-benzothiophen-3-yl)-2-(tert-butoxy)acetate

生成物 1

HCID 70813776methyl 2-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-benzothiophen-3-yl]acetate収率 55.5%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 2-(2-bromo-1-benzothiophen-3-yl)-2-(tert-butoxy)acetate (4c) (40 mg, 0.11 mmol) in N,N-dimethylformamide (2 mL) were successively added sodium carbonate (13 mg, 0.12 mmol), water (500 μL), palladium tetrakis(triphenylphosphine) (18.3 mg, 0.016 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (29 mg, 0.11 mmol). The mixture was heated at 100° C. for 2 hours. After cooling to room temperature, water (10 mL) was added. The aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (4d) as a white solid (25 mg, 0.061 mmol, 55%).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

出典と根拠

ORDレコード
ord-0aaf0e1a204a43dbb719e44fcf4c50bd
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238026B2

反応ノート

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