Triethylsilane → HCID 66862732, compound

HRID 253201Notes

Reaction equation

HRID 253201 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10]([CH:12]1[C:21](=O)[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[CH:18][CH:19]=2)[CH2:14][S:13]1)=[O:11]>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10]([CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[CH:18][CH:19]=2)[CH2:14][S:13]1)=[O:11]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 66862364HCID 66862364, compound

Product 1

HCID 66862732HCID 66862732, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (8.08 mmol, 0.94 g) was added to a solution of 7-methoxy-isothiochroman-4-one-3-carboxylic acid methyl ester (0.51 g, 2.02 mmol) in trifluoroacetic acid (15 mL) at room temperature under N2. The reaction was allowed to stir at room temperature for 2 h and was concentrated under reduced pressure. The resulting oil was dissolved in EtOAc (100 mL) and washed with sat. NaHCO3 (3×75 mL). The organic extracts were combined, dried (MgSO4) and concentrated to provide an oil. The oil was purified on silica using medium pressure chromatography (9:1 petroleum ether/EtOAc) to provide 7-methoxy-isothiochroman-3-carboxylic acid methyl ester (0.34 g, 70%) as a pale yellow oil. 1H-NMR (300 MHz, CDCl3) δ 3.14 (m, 2H), 3.58-3.63 (d, J=15 Hz, 1H), 3.73-3.86 (m, 8H), 6.70 (d, J=3 Hz, 1H), 6.75 (dd, J=3, 9 Hz, 1H), 7.10 (d, J=9 Hz, 1H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe resulting oil was dissolved in EtOAc (100 mL)
  3. washwashed with sat. NaHCO3 (3×75 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto provide an oil
  7. customThe oil was purified on silica using medium pressure chromatography (9:1 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-80ae5b9078aa4761862b4d10b16c82d9
Source dataset
uspto-grants-2011_01
Patent number
US07872023B2

Reaction notes

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