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Ethyl Acetate → 4-[2-(4-Bromo-phenyl)-2-methoxycarbonyl-ethyl]-benzoic acid tert-butyl ester

HRID 1401891
ノート
印刷プレビュー

反応式

HRID 1401891 の反応式
C(O[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1C)(=O)C.[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25]I)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:38]([O:41][CH2:42]C)(=[O:40])[CH3:39]>C1COCC1.O>[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:39]([C:5]2[CH:6]=[CH:7][C:8]([Br:11])=[CH:9][CH:10]=2)[C:38]([O:41][CH3:42])=[O:40])=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]
参加物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 8857Ethyl AcetateHCID 2733832Lithium hexamethyldisilazaneHCID 600267744-Bromo-2-methylphenyl acetateHCID 672121184-Iodomethyl benzoic acid tert-butyl ester

生成物 1

HCID 672113474-[2-(4-Bromo-phenyl)-2-methoxycarbonyl-ethyl]-benzoic acid tert-butyl ester収率 100%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 246.63 g of methyl-4-bromophenyl acetate and 342.54 g of 4-Iodomethyl benzoic acid tert-butyl ester in THF (1233 mL) was cooled to −8° C. A solution of lithium hexamethyl disilazide in THF (1185 mL, 1.0 M) was added dropwise ensuring that the temperature remaine below −2° C. After the addition was complete, the reaction was allowed to proceed for ˜45 min at the same temperature and then poured over a stirring mixture of ethyl acetate (2.46 L) and water (1.23 L). The organic phase was washed with saturated ammonium chloride and then with water. Dried over magnesium sulfate and concentrated under reduced pressure to obtain 450.5 g (100% yield) thick oil. HNMR: CDCl3, 1.41 (s, 9H), 2.88-2.90 (m, 1H), 3.24-3.28 (m, 1H), 3.45 (s, 3H), 3.63 (t, 1H). 6.96-6.99 (m, 4H), 7.25 (d, 2H), 7.68 (d, 2H)

後処理

  1. customremaine below −2° C
  2. additionAfter the addition
  3. washThe organic phase was washed with saturated ammonium chloride
  4. dry with materialDried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6d779bdda11245fc89438c93af105045
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08907103B2

反応ノート

読み込み中…

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