Water → 6-Hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-8-carbaldehyde

HRID 2103041ノート

反応式

HRID 2103041 の反応式
[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[CH:12]=[C:11]2[C:3]=1[CH2:4][CH2:5][C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1.[CH3:17][O:18]C(Cl)Cl.O>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[OH:15][C:14]1[C:2]([CH3:1])=[C:3]2[C:11](=[C:12]([CH:17]=[O:18])[C:13]=1[CH3:16])[O:10][C:6]1([CH2:7][CH2:8][CH2:9]1)[CH2:5][CH2:4]2

参加物

6

反応物 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 115502985,7-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol

生成物 1

HCID 866054876-Hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-8-carbaldehyde

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a cooled solution of 5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (1 g) in DCM (20 mL) was added TiCl4 (0.53 mL) which turned the solution a red color. To the solution was added dichloromethyl methyl ether (0.42 mL) and stirred at 0° C. for 30 min and then at room temperature for 30 min. The solution was poured into water and the DCM was separated, dried and evaporated. The residue was purified by silica gel column eluting with 20% ethylacetate in hexane to give 700 mg of 6-hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-8-carbaldehyde as a yellow solid.

後処理

  1. waitat room temperature for 30 min
  2. customthe DCM was separated
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel column
  6. washeluting with 20% ethylacetate in hexane

出典と根拠

ORDレコード
ord-067d23ddd9454e42b893dfa94e086972
出典データセット
uspto-grants-2009_08
特許番号
US07576094B2

反応ノート

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