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

HRID 1264055Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-3a8c27ca7c534e3bbfa515ddfa1efb59
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541481B2

Reaction notes

Loading…