Citric Acid → HCID 69712966, compound

HRID 2416564Notes

Reaction equation

CC(C[AlH]CC(C)C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[CH:24]=[O:25])=[CH:18][CH:17]=1.CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[N:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][CH2:24][OH:25])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

DIBAL (1.0 M in THF, 18.0 mL) was added over 10 min to a −78° C. suspension of (2E)-3-[4-(2-pyrimidinyl)phenyl]-2-propenal (2.50 g, 11.89 mmol, prepared as described in Reference Example 2) in dichloromethane (100 mL). The resulting suspension was stirred for 30 min at −78° C., methanol (2 mL) was added cautiously, and stirring was continued for 5 min at −78° C. The mixture was poured into a mixture of 10% aq. citric acid (300 mL) and dichloromethane (200 mL) and allowed to stir for 1 h. The organic layer was separated, washed with sat. aq. NaHCO3 (200 mL) and brine (200 mL), dried (MgSO4), filtered through Celite, and concentrated. The resulting material was triturated with ether and dried in vacuo to provide 2.08 g (82%) of the title compound. MS 213 (M+H)+.

Workup

stirringstirring
waitwas continued for 5 min at −78° C
stirringto stir for 1 h
customThe organic layer was separated
washwashed with sat. aq. NaHCO3 (200 mL) and brine (200 mL)
dry with materialdried (MgSO4)
filtrationfiltered through Celite
concentrationconcentrated
customThe resulting material was triturated with ether
customdried in vacuo

Sources & evidence

ORD record: ord-3833d50a738a40a48756d9657b546ffd
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825172B2

Reaction notes

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