Carbon Dioxide → HCID 53642175, compound

HRID 1200046Notes

Reaction equation

Br[C:2]1[S:6][C:5]([CH:7]=[CH:8][C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:23](=[O:25])=[O:24].Cl>O.O1CCCC1>[S:13]1[C:9]([CH:8]=[CH:7][C:5]2[S:6][C:2]([C:23]([OH:25])=[O:24])=[CH:3][CH:4]=2)=[CH:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]1=2

Participants

Conditions

Temperature: -70 °C

Procedure

To a stirred, chilled (-70° C.) suspension of 2-[2-(5-bromo-2-thienyl)ethenyl]benzo[b]thiophene (15.6 g) and tetrahydrofuran (400 ml) was added n-butyl lithium (21.4 ml of a 2.5M solution in hexanes), under nitrogen over 10 mins. The solution was stirred at -70° C. for 1.5 hr, and was transferred via canula to a flask containing a suspension of dry ice (excess) and tetrahydrofuran (1000 ml). The suspension was stirred for 2 hrs and allowed to warm to room temperature overnight. The mixture was poured into water (500 ml), acidified with hydrochloric acid, and the tetrahydrofuran was removed in vacuo. The resulting suspension was filtered, and the filter cake was washed with water and dried in vacuo overnight. The filter cake was recrystallized from dimethyl sulfoxide/10% hydrochloric acid to yield 10.5 g (75%) of product, mp 236°-237° C.

Workup

temperatureTo a stirred, chilled
customwas transferred via canula to a flask
additioncontaining
stirringThe suspension was stirred for 2 hrs
temperatureto warm to room temperature overnight
customthe tetrahydrofuran was removed in vacuo
filtrationThe resulting suspension was filtered
washthe filter cake was washed with water
customdried in vacuo overnight
customThe filter cake was recrystallized from dimethyl sulfoxide/10% hydrochloric acid

Sources & evidence

ORD record: ord-001407325e0a4206996fc59e29645b69
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04904674

Reaction notes

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