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Water → Methyl 2-[(2'-Methoxycarbonylbiphenyl-4-yl)methyl]-3-oxoheptanoate

HRID 865001
ノート
印刷プレビュー

反応式

HRID 865001 の反応式
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([O:30][CH3:31])=[O:29])=[CH:18][CH:17]=1.O>C1COCC1.C(O)(=O)C>[CH3:31][O:30][C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH:3]([C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5])=[CH:21][CH:20]=1)=[O:29]
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 962WaterHCID 24758Sodium hydrideHCID 546075Methyl 3-oxoheptanoateHCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

生成物 1

HCID 10738674Methyl 2-[(2'-Methoxycarbonylbiphenyl-4-yl)methyl]-3-oxoheptanoate収率 93%

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
溶媒
HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Under nitrogen atmosphere, 2.3 of methyl 3-oxoheptanoate, dissolved into 10 ml of anhydrous THF were dropped into a suspension containing 0.22 g of 80% NaH in 30 ml g of anhydrous THF. After the effervescence was over, 2.22 g of 4-bromomethyl-2'-methoxycarbonylbiphenyl, dissolved in 10 ml of anhydrous THF, were slowly dropped into the clear solution. After 15 minutes, water was added and acetic acid was added till acidic pH. The reaction mixture was extracted with AcOEt. The organic phase was washed with a NaCl saturated solution, dried on Na2SO4 and evaporated to dryness. The residue was purified by FC (eluent: hexane/AcOEt 8:2). 2.6 g of a clear oil were obtained (yield 93%); 1H-NMR (200 MHz, CDCl3)δ: 0.86 (t, 3H), 1.15-1.62 (m, 4H), 2.25-2.65 (m, 2H), 3.20 (d, 2H), 3.63 (s, 3H), 3.71 (s, 3H), 3.84 (t, 1H), 7.12-7.58 (m, 7H), 7.78 (dd, 1H).

後処理

  1. additionwere dropped into a suspension
  2. additionwere slowly dropped into the clear solution
  3. extractionThe reaction mixture was extracted with AcOEt
  4. washThe organic phase was washed with a NaCl saturated solution
  5. customdried on Na2SO4
  6. customevaporated to dryness
  7. customThe residue was purified by FC (eluent: hexane/AcOEt 8:2)

出典と根拠

ORDレコード
ord-653b84859dc94982ab5f2269628ea5a7
出典データセット
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05565464

反応ノート

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