Water → Methyl 4-(2-benzyloxybenzyl)benzoate

HRID 554532ノート

反応式

HRID 554532 の反応式
C([SiH](CC)CC)C.[CH3:8][O:9][C:10](=[O:33])[C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)O)=[CH:13][CH:12]=1.O>C(#N)C>[CH3:8][O:9][C:10](=[O:33])[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 962WaterHCID 12052TriethylsilaneHCID 21909317Methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoate

生成物 1

HCID 21909320Methyl 4-(2-benzyloxybenzyl)benzoate収率 62%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

In a nitrogen stream, triethylsilane (2.27 mL, 13.5 mmol) and a boron trifluoride-diethyl ether complex (1.52 mL, 11.88 mmol) were added to a solution of 4-[(2-benzyloxyphenyl)-hydroxymethyl]benzoic acid methyl ester (4.15 g, 11.9 mmol) in acetonitrile (22.7 mL) at −40° C. and the mixture solution was stirred at the same temperature for 1.5 hours and further at 0° C. for 30 minutes. Water was added thereto and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (2.39 g, 62%).

後処理

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)]

出典と根拠

ORDレコード
ord-f83c07b9920244398148734d25103fa4
出典データセット
uspto-grants-2011_11
特許番号
US08048897B2

反応ノート

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