Ethanol → HCID 59783788, compound

HRID 718042Notes

Reaction equation

HRID 718042 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=[C:8]([C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=3)[C:7]=2[CH:28]=1.B(Br)(Br)Br.C(O)C.CO>C(Cl)Cl.C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=[C:8]([C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=3)[C:7]=2[CH:28]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 25134Boron tribromideHCID 58388771HCID 58388771, compound

Product 1

HCID 59783788HCID 59783788, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of compound 34 (1.57 g, 4.21 mmol) in DCM (30 mL) was added BBr3 (1M in DCM, 13.0 mL, 13.0 mmol) at 4° C. drop wise and the reaction mixture was stirred for 2 h. Ethanol (20 mL) was added and the mixture was stirred at room temperature for 30 min. Enough MeOH to get everything soluble was added and this mixture was poured into ethyl acetate (600 mL). This organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography with 30% ethyl acetate in hexanes to afford title compound 35 (453 mg, 30%) as a beige solid. LRMS (ESI): (calc) 359.12. (found) 360.2 (MH)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. additionwas added
  3. washThis organic phase was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e6c82576e7b44844bd85bb5a804a4248
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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