2-(Trimethylsilyl)ethanol → HCID 54450278、化合物

HRID 1596692ノート

反応式

HRID 1596692 の反応式
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][C:16]([OH:18])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.[CH3:31][Si:32]([CH3:37])([CH3:36])[CH2:33][CH2:34]O>C(Cl)Cl>[CH3:31][Si:32]([CH3:37])([CH3:36])[CH2:33][CH2:34][O:17][C:16](=[O:18])[CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 180132-(Trimethylsilyl)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1013125210-Phenyl-3,6,9-trioxadecanoic acid

生成物 1

HCID 54450278HCID 54450278、化合物収率 97.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

10-Phenyl-3,6,9-trioxadecanoic acid (1.71 g, 6.71 mmol) was dissolved in CH2Cl2 (13.4 mL) and the solution was cooled to 0° C. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (1.41 g, 7.38 mmol) and N,N-dimethylaminopyridine (DMAP) (41.0 mg, 0.34 mmol) were added, and the suspension was stirred for 10 minutes at 0° C. 2-(Trimethylsilyl)ethanol (872.4 mg, 7.38 mmol) was added dropwise via syringe, and the solution was stirred for 20 minutes while warming to room temperature. The reaction was quenched with H2O and extracted with Et2O (3×50 mL). The combined Et2O extracts were washed sequentially with 10% HCl (1×50 mL), 5% NaHCO3 (1×50 mL), and saturated NaCl (1×50 mnL), and dried over Na2SO4. Concentration followed by flash chromatography (silica, 4:1 hexanes/EtOAc) afforded 10-phenyl-3,6,9-trioxadecanoic acid 2-(trimethylsilyl)ethyl ester (2.32 g, 97% yield). Rf=0.26 (4:1 hexanes/EtOAc); IR (neat): 3500-3400, 3000-2700, 1751, 1733, 1615, 1455, 1250, 1148, 1124 cm−1; 1H NMR (300 MHz, CDCl3): δ 7.32-7.23 (m, 5H), 4.54 (s, 2H), 4.24-4.18 (m, 2H), 4.10 (s, 2H), 3.72-3.59 (m, 8H), 1.01-0.95 (m, 2H), 0.01 (s, 9H); 13C NMR (75 MHz, CDCl3): δ 170.5, 138.2, 128.3, 127.6, 127.5, 73.2, 70.8, 70.6, 69.4, 68.8, 63.0, 17.3, −1.6; LRMS (LSIMS, 3-NBA): m/z 377.2 [M+Na+, calc'd for C18H30O5NaSi 377.5].

後処理

  1. stirringthe solution was stirred for 20 minutes
  2. temperaturewhile warming to room temperature
  3. customThe reaction was quenched with H2O
  4. extractionextracted with Et2O (3×50 mL)
  5. washThe combined Et2O extracts were washed sequentially with 10% HCl (1×50 mL), 5% NaHCO3 (1×50 mL), and saturated NaCl (1×50 mnL)
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration

出典と根拠

ORDレコード
ord-1e7fba038b4e43b1a9939815e468dee8
出典データセット
uspto-grants-2001_09
特許番号
US06291616B1

反応ノート

読み込み中…