Water → HCID 15448804, compound

HRID 324382Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]2[C:21]([CH:22]=[O:23])=[C:20]([OH:24])[CH:19]=[CH:18][C:10]=2[S:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].S(C1C=CC(C)=CC=1)(O[CH2:29][C@@H:30]1[O:32][CH2:31]1)(=O)=O.O>CN(C)C=O>[Cl:7][C:8]1[C:9]2[C:21]([CH:22]=[O:23])=[C:20]([O:24][CH2:29][C@@H:30]3[O:32][CH2:31]3)[CH:19]=[CH:18][C:10]=2[S:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium carbonate (2.62 g) was added to a stirred solution of ethyl 3-chloro-4-formyl-5-hydroxybenzo[b]thiophene-2-carboxylate (4.90 g, prepared as described above) in dry dimethylformamide (50 ml) and then a solution of (R)-glycidyl tosylate (4.12 g) in dry dimethyl formamide (50 ml) was added slowly. The mixture was then stirred at 60° C. for 3 hours, cooled and poured into water (1200 ml). The resulting pale-green solid was collected by filtration, washed with water (200 ml) and dried to give ethyl (R)-3-chloro-5-(2,3-epoxypropoxy)-4-formylbenzo[b]thiophene-2-carboxylate (5.15 g).

Workup

temperaturecooled
filtrationThe resulting pale-green solid was collected by filtration
washwashed with water (200 ml)
customdried

Sources & evidence

ORD record: ord-82388830b55545a7a89709ea5875a15d
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218405B1

Reaction notes

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