Triphenylphosphine → 4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-benzaldehyde

HRID 2215208ノート

反応式

HRID 2215208 の反応式
[CH:1]1([C:7]2[O:8][C:9]([CH3:15])=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([CH3:26])[C:24]=1O)[CH:20]=[O:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[O:8][C:9]([CH3:15])=[C:10]([CH2:12][CH2:13][O:14][C:24]3[C:23]([CH3:26])=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=3[CH3:16])[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 5363146Diisopropyl azodicarboxylateHCID 108567262-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethanol

生成物 1

HCID 219496594-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-benzaldehyde

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

0.400 g of the above prepared 2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethanol (1.91 mmol) was dissolved in 10 ml of toluene and treated successively at 0° C. with 0.287 g of 3,5-dimethyl-4-hydroxybenzaldehyde (1.91 mmol), 0.501 g of triphenylphosphine (1.91 mmol), and 0.387 g (1.91 mmol) of DIAD. The cooling bath was then removed and stirring continued for 2 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with dil. NaOH and water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=85/15) delivered finally 0.415 g of the title compound as colorless oil.

後処理

  1. customThe cooling bath was then removed
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with dil. NaOH and water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

出典と根拠

ORDレコード
ord-db13957a9f79408bbd893d8d1d2589c1
出典データセット
uspto-grants-2006_09
特許番号
US07109225B2

反応ノート

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