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Boron trifluoride etherate → 2-Phenoxy-3-(4-benzyloxynaphthalen-1-yl)-2-methylpropionic acid ethyl ester

HRID 348296
ノート
印刷プレビュー

反応式

HRID 348296 の反応式
[CH2:1]([O:3][C:4](=[O:34])[C:5]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:26])[CH:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:10][CH:9]=1)O)[CH3:2].B(F)(F)F.CCOCC.C([SiH](CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:34])[C:5]([O:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([CH3:26])[CH2:6][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:10][CH:9]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 693525693-(4Benzyloxynaphthalen-1-yl)-2-phenoxy-3-hydroxy-2-methylpropionic acid ethyl ester

生成物 1

HCID 693535002-Phenoxy-3-(4-benzyloxynaphthalen-1-yl)-2-methylpropionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

3-(4Benzyloxynaphthalen-1-yl)-2-phenoxy-3-hydroxy-2-methylpropionic acid ethyl ester (1.80 g, 3.9 mmol) in anhydrous CH2Cl2 (20 mL) was cooled to 0° C. and treated with BF3-Et2O (0.48 mL, 3.9 mmol, d=1.154) and triethylsilane (0.63 mL, 3.9 mmol, d=0.728). The mixture was stirred for 2 hr, gradually warming to ambient temperature. Saturated aqueous Na2CO3 (15 mL) was added and the mixture was stirred vigorously for 15 min. The solution was partitioned and the organic layer was washed twice with water and brine, dried over Na2SO4, and concentrated in vacuo to 3-(4-benzyloxynaphthalen-1-yl)-2-phenoxy-2-methylpropionic acid ethyl ester as a golden oil (1.55 g, 89%). Rf=0.41 (9:1 hexanes:ethyl acetate). 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J=8.3), 8.11 (d, 1H, J=8.3), 7.47 (d, 2H, J=7.8), 7.40 (t, 1H, J=8.3), 7.37 (t, 1H, J=8.3), 7.36 (t, 2H, J=7.8) 7.28 (d, 2H, J=7.8), 7.11 (t, 2H, J=8.8), 6.87 (t, 1H, J=7.8), 6.79 (d, 1H, J=7.8), 6.69 (d, 2H, J=8.8), 5.18 (s, 2H, 4.08 (q, 2H, J=7.0), 3.66 (d, 1H, J=14.4), 3.54 (d, 1H, J=14.4), 1.38 (s, 3H), 1.13 (t, 3H, J=7.0). MS [EI+] 458 (M+NH4)+

後処理

  1. stirringthe mixture was stirred vigorously for 15 min
  2. customThe solution was partitioned
  3. washthe organic layer was washed twice with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo to 3-(4-benzyloxynaphthalen-1-yl)-2-phenoxy-2-methylpropionic acid ethyl ester as a golden oil (1.55 g, 89%)

出典と根拠

ORDレコード
ord-57eca410dac6403fa4287d67cd1eedb3
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176224B2

反応ノート

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