Diisobutylaluminum hydride → 3-(4-Phenoxy-quinazolin-6-yl)-prop-2-en-1-ol

HRID 1264055ノート

反応式

HRID 1264055 の反応式
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[C:9]2[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[O:16]([C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH:5]=[CH:4][CH2:3][OH:2])[CH:7]=2)[N:12]=[CH:11][N:10]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 69259874HCID 69259874、化合物

生成物 1

HCID 694856033-(4-Phenoxy-quinazolin-6-yl)-prop-2-en-1-ol収率 73.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of ester 24 (1.35 g, 4.41 mmol) in toluene (60 mL) under N2 at −78° C. was added DIBAL-H (8.8 mL of a 1M solution in toluene, 8.8 mmol) dropwise. The reaction was then warmed to 0° C. and stirred for 30 minutes, then quenched with 30 mL of saturated Rochelle's salt and the mixture stirred overnight. The bilayer was transferred to a separatory funnel and the organic layer washed with H2O and brine and dried (MgSO4). After filtration the organic layer was concentrated under reduced pressure to provide a yellow oil which was purified by silica gel chromatography eluting with 1:1 hexanes:EtOAc, then EtOAc. The allylic alcohol 25 (900 mg, 73%) was isolated as a pale yellow oil. 1H NMR (CDCl3; 400 MHz): δ: 8.72 (s, 1 H), 8.27 (s, 1H), 7.66 (m, 2H), 7.62 (m, 1H), 7.47 (m, 3H), 7.34 (m, 1H), 7.24 (m, 2H), 6.82 (dd, 1h), 6.56 (m, 1H), 4.41 (dd, 1H).

後処理

  1. customquenched with 30 mL of saturated Rochelle's salt
  2. stirringthe mixture stirred overnight
  3. customThe bilayer was transferred to a separatory funnel
  4. washthe organic layer washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtration the organic layer
  7. concentrationwas concentrated under reduced pressure
  8. customto provide a yellow oil which
  9. customwas purified by silica gel chromatography
  10. washeluting with 1:1 hexanes

出典と根拠

ORDレコード
ord-3a8c27ca7c534e3bbfa515ddfa1efb59
出典データセット
uspto-grants-2003_04
特許番号
US06541481B2

反応ノート

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