2,3-Dihydrobenzofuran-5-carboxaldehyde → 2-Azido-3-(2,3-dihydro-benzofuran-5-yl)-acrylic acid methyl ester

HRID 1781319Notes

Reaction equation

CC(C)([O-])C.[K+].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=O)=[CH:15][C:10]=2[CH2:9][CH2:8]1.[N:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[N+:19]=[N-:20]>CO>[CH3:25][O:24][C:22](=[O:23])[C:21]([N:18]=[N+:19]=[N-:20])=[CH:16][C:14]1[CH:13]=[CH:12][C:11]2[O:7][CH2:8][CH2:9][C:10]=2[CH:15]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a cold (-10° C.) stirred solution of potassium tert-butoxide (6.06 g) in dry methanol (40 ml) was added dropwise a mixture of 2,3-dihydrobenzofuran-5-carboxaldehyde (2 g) and methyl azidoacetate (6.21 g). The mixture was stirred for 1 h at -10° C. and then stored at 0° C. for 18 h. The resulting pale yellow microcrystals were collected by filtration to give the title compound (3.12 g), m.p. 77°-80° C.

Workup

additionwas added dropwise
waitstored at 0° C. for 18 h
filtrationThe resulting pale yellow microcrystals were collected by filtration

Sources & evidence

ORD record: ord-d3d3361c405f4232a9008dac1542cd34
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05633276

Reaction notes

Loading…