Butyl methyl ether → Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoate

HRID 1893165

反応式

HRID 1893165 の反応式
P([O:8][CH2:9][CH3:10])(OCC)OCC.C[O:12][CH2:13][CH2:14]CC.[CH3:17][C:18](C)([O-:20])C.[K+].[CH2:23]([O:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.C(O)(C)(C)C>[CH2:18]([O:20][C:9](=[O:8])[C:10]([O:12][CH2:13][CH3:14])=[CH:35][C:34]1[CH:37]=[CH:38][C:31]([O:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:32][CH:33]=1)[CH3:17]

参加物

7

反応物 4

HCID 12338Butyl methyl etherHCID 31215Triethyl phosphiteHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 23665647Potassium tert-butoxide

生成物 1

HCID 54423854Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoate収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

P(OEt)3 was added dropwise to a mixture of tent-butyl methyl ether 55 mL) and potassium tert-butoxide (4.65 g, 41.4 mmol) under a nitrogen atmosphere at 20-30° C. 4-Benzyloxybenzaldehyde (4.61 g, 21.7 mmol) was added in portions to this mixture at 5° C. followed by the addition of tert-butyl alcohol (6.70 g). The reaction mixture was allowed to reach 15° C. and stirred at this temperature for approximately 30 min, after which the reaction was completed (as judged by TLC). Water (30 mL) was added at 5-10° C., and the phases were allowed to separate. The organic phase was concentrated in vacuo, and ethanol (30 mL) was added to the stirred solution. After crystallization had occurred, water (18 mL) was added to the suspension. The light-yellow title compound was filtered off, washed with ethanol/water (1:1 v/v), and dried in vacuo to yield 6.52 g (92% yield).

後処理

  1. customto reach 15° C.
  2. customto separate
  3. concentrationThe organic phase was concentrated in vacuo, and ethanol (30 mL)
  4. additionwas added to the stirred solution
  5. customAfter crystallization
  6. additionwater (18 mL) was added to the suspension
  7. filtrationThe light-yellow title compound was filtered off
  8. washwashed with ethanol/water (1:1 v/v)
  9. customdried in vacuo
  10. customto yield 6.52 g (92% yield)

出典と根拠

ORDレコード
ord-61d528ca74cd4b48a02921468bcf1878
出典データセット
uspto-grants-2013_08
特許番号
US08513233B2

関連ノート

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