Hydride → (R)-6-Bromo-11-[3,5-dibromo-4-(1-hydroxymethyl-2-phenyl-ethoxy)-phenyl]-benzo[b]naphtho[2,3-d]thiophene

HRID 1873200

反応式

HRID 1873200 の反応式
[Br:1][C:2]1[CH:20]=[C:19]([C:21]2[C:30]3[C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[S:33][C:29]=3[C:28]([Br:38])=[C:27]3[C:22]=2[CH:23]=[CH:24][CH:25]=[CH:26]3)[CH:18]=[C:17]([Br:39])[C:3]=1[O:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](OC)=[O:7].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-]>C1COCC1>[Br:38][C:28]1[C:29]2[S:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[C:30]=2[C:21]([C:19]2[CH:18]=[C:17]([Br:39])[C:3]([O:4][C@@H:5]([CH2:6][OH:7])[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:2]([Br:1])[CH:20]=2)=[C:22]2[C:27]=1[CH:26]=[CH:25][CH:24]=[CH:23]2

参加物

5

反応物 3

HCID 166653HydrideHCID 731089432-[2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-3-phenyl-propionic acid, methyl esterHCID 86605258Lithium aluminum hydride aluminum chloride

生成物 1

HCID 53810433(R)-6-Bromo-11-[3,5-dibromo-4-(1-hydroxymethyl-2-phenyl-ethoxy)-phenyl]-benzo[b]naphtho[2,3-d]thiophene収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of R)-2-[2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11 -yl)-phenoxy]-3-phenyl-propionic acid, methyl ester (0.30 g, 0.414 mmol) in THF (4.2 mL) was added dropwise to a -78 ° C., stirred solution of mixed hydride (0.435 mL, 0.414 mmol) of lithium aluminum hydride/aluminum chloride (1.0 M solution in THF) in THF (3 mL) under a dry nitrogen atmosphere over a period of 5 min. After 1 h., the solution was allowed to warm to ambient temperature. After 2 h. the reaction mixture was quenched carefully with methanol (3 mL) and further diluted with water (80 mL). Aqueous mixture was extracted with ethyl acetate (2×80 mL). The ethyl acetate extracts were washed with water, dried with brine and anhydrous MgSO4, and concentrated to provide the title compound as a white solid (0.28 g, 97%): mp 83-85: MS (EI): [M+], 3 bromine isotope pattern, 694, 696, 698, 700.

後処理

  1. customAfter 2 h. the reaction mixture was quenched carefully with methanol (3 mL)
  2. additionfurther diluted with water (80 mL)
  3. extractionAqueous mixture was extracted with ethyl acetate (2×80 mL)
  4. washThe ethyl acetate extracts were washed with water
  5. dry with materialdried with brine and anhydrous MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d42269e21be45f580e504096dc023da
出典データセット
uspto-grants-2000_08
特許番号
US06110962

関連ノート

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