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

HRID 2103041노트

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HRID 2103041 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-067d23ddd9454e42b893dfa94e086972
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576094B2

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