3,4-dihydro-2H-pyran → 8-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-one

HRID 2099388

반응식

HRID 2099388 반응식
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S([O-])(=O)=O)=[CH:9][CH:8]=1.[NH+]1C=C[CH:21]=[CH:20][CH:19]=1.[Cr](Cl)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[C:35]([O-])(=[O:37])C.[Na+]>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:37][CH2:35][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[C:17](=[O:25])[CH2:21][CH2:20][CH2:19]2

참가 물질

6

반응물 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 517045Sodium AcetateHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 219860898-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-one수율 55%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

The diol (Intermediate H3) (2.42 g, 13.5 mmol) was dissolved in CH2Cl2 (75 mL) and reacted with dihydropyran (1.3 mL, 13.8 mmol) and pyridinium para-toluene sulfonate (PPTS) (350 mg, 1.36 mmol) at rt for 18 h. The mixture was concentrated onto SiO2 and purified by chromatography with 10% EtOAc:Hx. The tetrahydropyranyl (THP) protected alcohol (2.02 g, 7.70 mmol) was dissolved in CH2Cl2 (10 mL) and added to a mixture of pyridinium chlorochromate (PCC) (4.9 g, 22.2 mmol), sodium acetate (310 mg, 3.56 mmol) and celite (110 g) in CH2Cl2 (100 mL). The mixture was reacted at rt for 18 h and filtered through celite. The residue was purified by chromatography on SiO2 with 20 to 30% EtOAc:Hx to yield 8-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-one (Intermediate H4) (˜55%).

후처리

  1. concentrationThe mixture was concentrated onto SiO2
  2. custompurified by chromatography with 10% EtOAc
  3. customThe mixture was reacted at rt for 18 h
  4. filtrationfiltered through celite
  5. customThe residue was purified by chromatography on SiO2 with 20 to 30% EtOAc

출처 및 근거

ORD 기록
ord-f6c33da865724e7bb937be9df4336487
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569584B2

연결된 노트

불러오는 중…