3-Furaldehyde → HCID 10666472, compound

HRID 1033102Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1Br.[Li][CH2:22][CH2:23]CC.O1[CH:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27]1>C1COCC1.CCCCCC>[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[CH:31]([OH:32])[C:28]1[CH:29]=[CH:30][CH:23]=[CH:22][CH:27]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 2-bromo-5-benzyloxybenzaldehyde dimethylacetal (Tet. Lett., 22, 5027 (1981)) (130 g) in THF (2.0 L), cooled to -78° C., was added dropwise a solution of n-BuLi (210 ml, 1.91M) in hexane. After 15 min., a solution of 3-furaldehyde (26.7 mL) in THF (50 ml) was added dropwise. The cooling bath was removed, then the reaction mixture was warmed slowly (40 min.) to -10° C. and quenched with a saturated NH4Cl solution. The reaction mixture was diluted with Et2O (2.0 L). The organic phase decanted, washed with H2O (3×), brine, dried over MgSO4, and the solvents evaporated. The residue was chromatographed on silica gel (hexane/EtOAc 95:5 to 85:15) to give the title product as a foam.

Workup

customThe cooling bath was removed
customquenched with a saturated NH4Cl solution
additionThe reaction mixture was diluted with Et2O (2.0 L)
customThe organic phase decanted
washwashed with H2O (3×), brine
dry with materialdried over MgSO4
customthe solvents evaporated
customThe residue was chromatographed on silica gel (hexane/EtOAc 95:5 to 85:15)

Sources & evidence

ORD record: ord-d8351610d4204990a3911ab14c8fc6e9
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05308852

Reaction notes

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