Diisobutylaluminum hydride → HCID 71281829, compound

Temperature

-78 °C

To solution of ethyl 2-bromo-6-methyl-6H-thieno[2,3-b]pyrrole-5-carboxylate (5.47 g, 18.28 mmol) in DCM (55 mL) at −78° C. was added solution of DIBAL-H (1M hexanes, 42.00 mL, 42.00 mmol). Reaction mixture was stirred 30 min at −78° C. before it was quenched with Na—K-tartrate (aqueous saturated, 50 mL). Mixture was allowed to warm to room temperature and was stirred 1 h. Product was extracted with DCM (3×100 mL). Organic phase was washed with NaCl (aqueous saturated, 50 mL) and dried over Na2SO4. Solvent was concentrated to yield (2-bromo-6-methyl-6H-thieno[2,3-b]pyrrol-5-yl)methanol (4.55 g, 97%) as solid which was used in the next step without purification.

1. customReaction mixture
2. customwas quenched with Na—K-tartrate (aqueous saturated, 50 mL)
3. temperatureto warm to room temperature
4. stirringwas stirred 1 h
5. extractionProduct was extracted with DCM (3×100 mL)
6. washOrganic phase was washed with NaCl (aqueous saturated, 50 mL)
7. dry with materialdried over Na2SO4
8. concentrationSolvent was concentrated

ORD record

ord-b4dd0e882ced4e38b9b9f897941dbca8

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409905B2