Tetrahydrofuran → HCID 68535847, compound

HRID 1453954Notes

Reaction equation

HRID 1453954 reaction equation
[N+:1]([C:4]1[C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=[CH:6][N:5]=1)([O-:3])=[O:2].[O:12]1CCCC1>>[OH:12][CH2:11][CH2:10][C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 59006385HCID 59006385, compound

Product 1

HCID 68535847HCID 68535847, compound

Procedure

Dimethyl sulfide-borane complex (15.9 mL, 32 mmol) was added to a solution of 2-nitro-3-vinylpyridine (2.4 g, 15.9 mmol) (Yamaka et. al., Heterocycles, 1992, 34, 2379-2384) in tetrahydrofuran (30 mL) under argon. The reaction was stirred at 200C for 2 h, and concentrated in vacuo. The concentrate was redissolved in tetrahydrofuran and stirred overnight with 20% aqueous sodium hydroxide (20 mL) and 30% hydrogen peroxide solution (20 mL). Methylene chloride was added and the mixture extracted with saturated sodium bicarbonate, and the organic phase dried over sodium sulfate. The crude product was purified (silica gel, 0-50% ethyl acetate in hexane gradient elution) to produce the title compound (0.300 g). MS 169 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe concentrate was redissolved in tetrahydrofuran
  3. additionMethylene chloride was added
  4. extractionthe mixture extracted with saturated sodium bicarbonate
  5. dry with materialthe organic phase dried over sodium sulfate
  6. customThe crude product was purified
  7. wash(silica gel, 0-50% ethyl acetate in hexane gradient elution)

Sources & evidence

ORD record
ord-67511701055f4e4f8dc82e775d877aef
Source dataset
uspto-grants-2009_01
Patent number
US07476665B2

Reaction notes

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