Hydrochloric Acid → HCID 10038048, compound

HRID 2113657Notes

Reaction equation

HRID 2113657 reaction equation
[CH2:1]([C:3]1[C:4](=[O:20])[CH2:5][C:6]2([CH2:18][CH3:19])[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:16]C)[CH:12]=3)[C:7]=12)[CH3:2].B(Br)(Br)Br.Cl>C(Cl)Cl.C(OCC)C>[CH2:1]([C:3]1[C:4](=[O:20])[CH2:5][C:6]2([CH2:18][CH3:19])[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=3)[C:7]=12)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 58604064HCID 58604064, compound

Product 1

HCID 10038048HCID 10038048, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,3a-diethyl-7-methoxy-3,3a,4,5-tetrahydro-2H-cyclopenta[α]naphthalen-2-one (10 mg, 0.036 mmol) in anhydrous CH2Cl2 (0.36 mL) was cooled in an ice bath, stirred under a N2 atmosphere, and treated with 1M BBr3 in CH2Cl2 (0.11 mL, 0.11 mmol). The resulting yellow suspension was stirred at 0-5° C. for 170 minutes and then treated with 1N HCl in diethyl ether (0.20 mL). The resulting mixture was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 1:1 hexane-EtOAc. The UV visible product band was eluted with 5% methanol in CH2Cl2 and the eluant was evaporated under vacuum to afford 1,3a-diethyl-7-hydroxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as a white solid.

Workup

  1. stirringThe resulting yellow suspension was stirred at 0-5° C. for 170 minutes
  2. customThe resulting mixture was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.)
  3. washThe UV visible product band was eluted with 5% methanol in CH2Cl2
  4. customthe eluant was evaporated under vacuum

Sources & evidence

ORD record
ord-48b1ef1f41684620a8562207cb2bfcf3
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

Loading…