Benzaldehyde, 4-(phenylmethoxy)- → HCID 12134921, compound

HRID 1893170Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[CH2:9]([O:11][C:12](=[O:22])[CH:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:14])[CH3:10].[CH2:23]([O:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[CH2:9]([O:11][C:12](=[O:22])[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])[CH:35]([C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:38][CH:37]=1)[OH:36])[CH3:10]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of lithium diisopropylamide (LDA) (26 mL, 52 mmol, 2 M in tetrahydrofuran) was cooled to −78° C. and then added to a solution of 2-Phenoxypropionic acid ethyl ester (10 g, 51 mmol) in anhydrous tetrahydrofuran (THF) (80 mL) also cooled to −78° C. under an atmosphere of nitrogen. After 30 min, 4-benzyloxybenzaldehyde (10 g, 47 mmol) was added in one portion. After stirring over night, the reaction mixture was quenched with saturated solution of aqueous NH4Cl (10 mL) and the mixture allowed to warm to ambient temperature. The biphasic mixture was diluted with dichloromethane and partitioned, and the organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified in silica to provide colorless oil (8.9 g, 47%), Rf=0.30 in 10:1 ethyl acetate: petroleum ether.

Workup

customthe reaction mixture was quenched with saturated solution of aqueous NH4Cl (10 mL)
temperatureto warm to ambient temperature
additionThe biphasic mixture was diluted with dichloromethane
custompartitioned
washthe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified in silica

Sources & evidence

ORD record: ord-481eceaed10d45ae847cdb6e7af7d80d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513233B2

Reaction notes

Loading…