Triphenylphosphine → 5-(tetrahydro-2H-pyran-4-yloxy)indan-1-one

HRID 2252260

反応式

HRID 2252260 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[O:12]1[CH2:17][CH2:16][CH:15](O)[CH2:14][CH2:13]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[O:12]1[CH2:17][CH2:16][CH:15]([O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH2:14][CH2:13]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 2331475-Hydroxy-1-indanoneHCID 5387121Dibenzyl azodicarboxylate

生成物 1

HCID 692013445-(tetrahydro-2H-pyran-4-yloxy)indan-1-one収率 85.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-Hydroxy-1-indanone (0.636 g, 4.30 mmol), tetrahydro-pyran-4ol (1.22 mL, 12.80 mmol), PPh3-polymer supported (2.864 g, 8.59 mmol), DBAD (1.978 g, 8.59 mmol) and THF (40 mL) were mixed, and shaken overnight. The mixture was filtered, and washed with THF (10 mL×3). The filtrate was concentrated. The residue was purified by flash chromatography to give the above intermediate (0.85 g, 85%). MS (APCI) m/z 233 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 1.79-1.89 (m, 2H) 2.01-2.12 (m, 2H) 2.62-2.69 (m, 2H) 3.07-3.15 (m, 2H) 3.85-4.00 (m, 4H) 4.75 (m, 1H) 6.97 (dd, J=8.65, 2.20 Hz, 1H) 7.08 (s, 1H) 7.63 (d, J=8.48 Hz, 1H).

後処理

  1. additionwere mixed
  2. filtrationThe mixture was filtered
  3. washwashed with THF (10 mL×3)
  4. concentrationThe filtrate was concentrated
  5. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-236c599371b04e038cd9929e46b28abb
出典データセット
uspto-grants-2008_01
特許番号
US07320986B2

関連ノート

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