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

HRID 661963

反応式

HRID 661963 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7c3e76a7c3c64a4fb31163df383f1410
出典データセット
uspto-grants-2011_12
特許番号
US08084620B2

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