Dichloromethane → 3-[2(E)-(2-Pyridyl)ethenyl]benzyl alcohol

HRID 1198565

Reaction equation

ClC1C=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH2:17][OH:18])=[N:9]2)=CC=1.CC(C[AlH]CC(C)C)C.ClCCl>C1(C)C=CC=CC=1>[N:9]1[CH:10]=[CH:5][CH:6]=[CH:7][C:8]=1/[CH:12]=[CH:13]/[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][OH:18]

Participants

Conditions

Temperature: -70 °C

Procedure

The methyl benzoate (Example 37b part ii) (2.25 g, 9.4 mmol) was dissolved in dry toluene (60 ml) and cooled to -70° C. under nitrogen. 1M DIBAL in dichloromethane (18.8 ml, 18.8 mmol) was added over 15 minutes and the reaction mixture allowed to warm up to -30° C. for 30 minutes. The reaction was quenched by careful addition of methanol (8 ml), then water, and after filtration through Celite the organic phase was evaporated in vacuo.

Workup

temperatureto warm up to -30° C. for 30 minutes
customThe reaction was quenched by careful addition of methanol (8 ml)
filtrationwater, and after filtration through Celite the organic phase
customwas evaporated in vacuo

Sources & evidence

ORD record: ord-f12ccb71f6ac4577a2b2f68c674ebacb
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281593

Linked notes

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