Lilial → (E)-3(2-Hydroxy-phenyl)-acrylic acid 3(4-tert-butyl-phenyl)-1-ethoxy-propyl ester

HRID 655078

反応式

HRID 655078 の反応式
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])(C)(C)C.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](C)=[CH:32][O:33][CH2:34][CH3:35])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].C(C1C=CC(CC(C)C=O)=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C1COCC1.CC1C=CC(S(O)(=O)=O)=CC=1>[C:20]([C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][CH:32]([O:17][C:15](=[O:16])/[CH:14]=[CH:13]/[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[OH:6])[O:33][CH2:34][CH3:35])=[CH:28][CH:29]=1)([CH3:23])([CH3:21])[CH3:22]

参加物

7

反応物 3

HCID 228987LilialHCID 22290462(E)-3-[2(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acidHCID 540774831-Tert-butyl-4-(3-ethoxy-2-methyl-allyl)-benzene

生成物 1

HCID 68523215(E)-3(2-Hydroxy-phenyl)-acrylic acid 3(4-tert-butyl-phenyl)-1-ethoxy-propyl ester収率 28.2%

試薬・触媒・溶媒 3

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3.1 g of (E)-3-[2-(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid, 3.0 g of 1-tert-butyl-4-(3-ethoxy-2-methyl-allyl)-benzene, accessible from 3-(4-tert-butyl-phenyl)-2-methyl-propionaldehyde via a two step procedure according to P. D. Bartlett and A A. Frimer, Heterocycles 11, 419-435, (1978), and 20 mg of p-TSA in 25 ml of toluene was stirred at 0° C. for 4 h and at room temperature for 14 h. The reaction mixture was partitioned between saturated sodium carbonate and hexane and the organic layer was washed with brine, dried over (Na2SO4) and evaporated to dryness to yield 5.3 g of the crude intermediate (E)-3-[2-(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid 3-(4-tert-butyl-phenyl)-1-ethoxy-propyl ester as a pale yellow oil. This was dissolved in 20 ml of THF and treated at 0° C. with 3.2 g of solid TBAF-3H2O. After 30 min., the mixture was concentrated and purification by repeated flash chromatography yielded 1.2 g of the title ester (a mixture of diastereoisomers) as a pale yellow oil.

後処理

  1. customThe reaction mixture was partitioned between saturated sodium carbonate and hexane
  2. washthe organic layer was washed with brine
  3. dry with materialdried over (Na2SO4)
  4. customevaporated to dryness
  5. customto yield 5.3 g of the crude intermediate (E)-3-[2-(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid 3-(4-tert-butyl-phenyl)-1-ethoxy-propyl ester as a pale yellow oil
  6. concentrationthe mixture was concentrated
  7. custompurification by repeated flash chromatography

出典と根拠

ORDレコード
ord-5fc8dd8969f5410f93583b2e57cc2393
出典データセット
uspto-grants-2011_12
特許番号
USRE043006E1

関連ノート

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