Isobutanol → 4-Isobutoxy-benzo[b]thiophene

HRID 1929236Notes

Reaction equation

HRID 1929236 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([OH:10])=[CH:7][CH:8]=[CH:9][C:2]1=2.[CH2:11](O)[CH:12]([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[CH2:11]([O:10][C:6]1[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[CH:9]=[CH:8][CH:7]=1)[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 6560IsobutanolHCID 11776TriphenylphosphineHCID 19217Benzo(b)thiophen-4-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 596002244-Isobutoxy-benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Benzo[b]thiophen-4-ol (200, 4.3 g, 28.9 mmol) and iso-butanol (3.2 ml, 34.7 mmol) are dissolved under argon in 150 ml of toluene. After addition of triphenylphosphine (9.1 g, 34.7 mmol) and a 40% solution of DEAD in toluene (16.8 ml, 34.7 mmol), the mixture is stirred at 120° C. over night. After cooling down, the reaction mixture is subsequently washed with saturated aqueous NaHCO3 solution and NaCl solution, dried over Na2SO4 and evaporated under reduced pressure. Triphenylphosphinoxid is removed by crystallization from ethyl acetate and hexane and the crude product is further purified by flash chromatography (silica gel, hexane/ethyl acetate 9:1).

Workup

  1. temperatureAfter cooling down
  2. washthe reaction mixture is subsequently washed with saturated aqueous NaHCO3 solution and NaCl solution
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customTriphenylphosphinoxid is removed by crystallization from ethyl acetate and hexane
  6. customthe crude product is further purified by flash chromatography (silica gel, hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-4846635a5a5b4d2384a7fb297f53567e
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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