Benzo(B)Thiophene → HCID 90094984, compound

HRID 627463Notes

Reaction equation

HRID 627463 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[S:9][CH:8]=[CH:7][C:5]=2[CH:6]=1.CC([O-])(C)C.[K+].[SiH:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18]>O1CCCC1>[S:9]1[CH:8]=[C:7]([Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]1=2

Participants

5

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 12052TriethylsilaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 90094984HCID 90094984, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was conducted according to the General Procedure by heating thianaphthene (66 mg, 0.5 mmol, 1 equiv.), KOt-Bu (8.4 mg, 0.08 mmol, 0.15 equiv.) and Et3SiH (239 microliters, 1.5 mmol, 3 equiv.) in 1 mL of tetrahydrofuran for 50 hours at 23° C. After aqueous work up, the crude reaction mixture was purified by chromatography on silica eluting with 80:2 hexanes:triethylamine to obtain 103 mg (83%) of the title compound as a colourless oil. 1H NMR (500 MHz, THF-d8) δ 7.90-7.85 (m, 1H), 7.84-7.76 (m, 1H), 7.53 (d, J=0.8 Hz, 1H), 7.34-7.20 (m, 2H), 1.08-0.99 (m, 9H), 0.95-0.80 (m, 6H). 13C NMR (126 MHz, THF-d8) δ 144.78, 142.34, 139.12, 132.97, 125.10, 124.84, 124.34, 122.91, 7.84, 5.10. HRMS: [C14H20SSi] calculated 248.1051, measured 248.1055. The HSQC spectrum of this reaction product as provided in FIG. 14.

Workup

  1. customAfter aqueous work up, the crude reaction mixture
  2. customwas purified by chromatography on silica eluting with 80:2 hexanes

Sources & evidence

ORD record
ord-2e62f5f1fe13448a938e52e6a163d590
Source dataset
uspto-grants-2016_04
Patent number
US09309269B2

Reaction notes

Loading…