Hydrochloric Acid → HCID 18546167, compound

HRID 1267324Notes

Reaction equation

CS(C)=O.[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:21][C:19]=2[N:20]=1.C(N(CC)CC)C.Cl>ClCCl>[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:15][C:16]1[O:17][C:18]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]=[O:28])=[CH:21][C:19]=2[N:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Oxalyl chloride[(COCl)2] (0.88 g) was added dropwise to a solution of dimethyl sulfoxide (DMSO) (1.0 g) in dichloromethane (30 ml) at −30° C. To the mixture was added 3-[2-(2-naphthylmethyl)benzoxazol-5-yl]-propanol (2.0 g). The mixture was stirred for 30 minutes at the same temperature. To the mixture was added triethyl amine (3.19 g). The mixture was stirred for 30 minutes, warmed to 0° C. and poured into 2N HCl. The organic layer was separated, washed with water and dried over magnesium sulfate (MgSO4). The solvent was distilled off, and the residue was subjected to silica gel column chromatography. From the fractions eluted with ethyl acetate-hexane (1:2, v/v), 3-[2-(2-naphthylmethyl)benzoxazol-5-yl]propionaldehyde (1.54 g, 77%) was obtained. Recrystallization from ether-isopropyl ether gave colorless needles. Melting point: 81-82° C.

Workup

stirringThe mixture was stirred for 30 minutes
customThe organic layer was separated
washwashed with water
dry with materialdried over magnesium sulfate (MgSO4)
distillationThe solvent was distilled off
washFrom the fractions eluted with ethyl acetate-hexane (1:2

Sources & evidence

ORD record: ord-06f74722ff444219819508e61ee04104
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552058B1

Reaction notes

Loading…