Triphenylphosphine → 4-[2-(2-tert-Butyl-5-methyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-7-carbaldehyde

HRID 2215197ノート

反応式

HRID 2215197 の反応式
[C:1]([C:5]1[O:6][C:7]([CH3:13])=[C:8]([CH2:10][CH2:11][OH:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O[C:15]1[C:23]2[CH:22]=[CH:21][S:20][C:19]=2[C:18]([CH:24]=[O:25])=[CH:17][CH:16]=1.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>[C:1]([C:5]1[O:6][C:7]([CH3:13])=[C:8]([CH2:10][CH2:11][O:12][C:15]2[C:23]3[CH:22]=[CH:21][S:20][C:19]=3[C:18]([CH:24]=[O:25])=[CH:17][CH:16]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 111829574-Hydroxy-benzo[b]thiophene-7-carboxaldehydeHCID 115792322-(2-Tert-butyl-5-methyl-oxazol-4-yl)-ethanol

生成物 1

HCID 219496634-[2-(2-tert-Butyl-5-methyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-7-carbaldehyde収率 47.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

0.800 g of the above prepared (example 1, step f]) 2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethanol (4.37 mmol) was dissolved in 25 ml of toluene and treated successively at 0° C. with 0.778 g of 4-hydroxy-benzo[b]thiophene-7-carbaldehyde (4.37 mmol), 1.145 g of triphenylphosphine (4.37 mmol), and 0.883 g (4.37 mmol) of DIAD. The cooling bath was then removed and stirring continued for 4 h. Pouring onto crashed ice, twofold extraction with EtOEt, washing with dil. NaOH and water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=6/4) and crystallization from EtOEt, produced finally 0.713 g of the title compound as off-white crystals of mp. 140–42° (dec.).

後処理

  1. customThe cooling bath was then removed
  2. additionPouring
  3. extractionice, twofold extraction with EtOEt
  4. washwashing with dil. NaOH and water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. customfollowed by flash chromatography (SiO2, hexane/AcOEt=6/4) and crystallization from EtOEt

出典と根拠

ORDレコード
ord-54aaed913ab3475ea9a329ac214ea9a4
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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