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2-Methyl-2-butene → 2-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetic acid

HRID 514142
ノート
印刷プレビュー

反応式

HRID 514142 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH:20]=[O:21])[C:3]=1[CH3:30].CC(=CC)C.P([O-])(O)(O)=[O:37].[Na+].Cl([O-])=O.[Na+].OS([O-])(=O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:4]([CH:19]([O:22][Si:23]([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:24])[CH3:25])[C:20]([OH:37])=[O:21])[C:3]=1[CH3:30]
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 5

HCID 105532-Methyl-2-buteneHCID 516919Sodium BisulfateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866915662-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetaldehyde

生成物 1

HCID 67126195
2-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A DCM solution (8.0 mL) of 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyl-oxy)acetaldehyde (0.65 g, 1.29 mmol) was combined with 2-methyl-2-butene (1.5 mL, 14.1 mmol), sodium dihydrogen phosphate (8.0 mL, 1.0 M) and sodium chlorite (1.37 g, 14.46 mmol) and stirred vigorously overnight. The mixture was diluted 200% with DCM, the acidity adjusted to pH<5 with 2 M NaHSO4 and extracted with DCM (3×20 mL). The extracts were combined dried and concentrated under vacuo. The crude mixture was observed to contain the desired carboxylic acid (0.741 g) according to 1H NMR analysis and was used without purification. 1H-NMR: (400 MHz, CD3OD): δ 8.35 (d, J=8.4 Hz, 1H); 7.58-7.51 (m, 3H); 7.46-7.44 (m, 1H); 7.39-7.33 (m, 1H); 7.31-7.22 (m, 2H); 5.33 (s, 1H); 2.72 (s, 3H); 0.825 (s, 9H); −0.03 (s, 3H); −0.26 (s, 3H).

後処理

  1. extractionextracted with DCM (3×20 mL)
  2. customThe extracts were combined dried
  3. concentrationconcentrated under vacuo
  4. customwas used without purification

出典と根拠

ORDレコード
ord-75aa18d60af2448f8695456d50952979
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102614B2

反応ノート

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