Phenol → 8-Phenoxy-1,4-dioxaspiro[4.5]decane

HRID 661963

반응식

HRID 661963 반응식
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[O:11]([CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

생성물 1

HCID 189804238-Phenoxy-1,4-dioxaspiro[4.5]decane수율 32%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Step 1 A solution of 1,4-dioxaspiro[4.5]decan-8-ol (1.00 g, 6.32 mmol), phenol (0.714 g, 7.59 mmol) and triphenylphosphine (1.824 g, 6.95 mmol) in DCM (21.07 mL) was treated with diisopropyl azodicarboxylate (1.48 mL, 7.59 mmol) and the mixture was stirred at rt for 5 days. The mixture was concentrated and the residue was purified by column chromatography, eluting with a gradient from hexane to 80:20 hexane-EtOAc). The crude product was dissolved in EtOAc and the solution was washed twice with 1 M aqueous sodium hydroxide and brine, dried and concentrated to provide 8-phenoxy-1,4-dioxaspiro[4.5]decane as a colorless liquid (0.468 g, 32%). 1H NMR (500 MHz, chloroform-d) δ 7.16-7.24 (2H, m), 6.81-6.89 (3H, m), 4.30-4.38 (1H, m), 3.85-3.93 (4H, m), 1.80-1.90 (6H, m), 1.50-1.59 (2H, m).

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography
  3. washeluting with a gradient from hexane to 80:20 hexane-EtOAc)
  4. dissolutionThe crude product was dissolved in EtOAc
  5. washthe solution was washed twice with 1 M aqueous sodium hydroxide and brine
  6. customdried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7c3e76a7c3c64a4fb31163df383f1410
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

연결된 노트

불러오는 중…