Ethanol → HCID 59783788, compound

HRID 1946575Notes

Reaction equation

HRID 1946575 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-30ea599cf95a43b5afc4d797c8d49f6e
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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