Triethylamine → HCID 11356643, compound

HRID 723638Notes

Reaction equation

HRID 723638 reaction equation
[S:1]1[CH:6]=[CH:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.FC(F)(F)S(O[Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])(=O)=O>C(Cl)Cl>[O:7]([C:4]1[CH:3]=[CH:2][S:1][CH2:6][CH:5]=1)[Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11804719HCID 11804719, compound

Product 1

HCID 11356643HCID 11356643, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dihydro-4H-thiopyran-4-one (1.50 g, 13.1 mmol, synthesized as described in Richards et al. J. Org. Chem. 46,4836–4842 (1981)) was dissolved in CH2Cl2 (130 mL) and triethylamine (5.47 mL, 39.4 mmol) was added. tert-Butyldimethylsilyl trifluoromethanesulfonate (3.62 mL, 15.8 mmol) was then added. After 10 minutes, the volatiles were removed in vacuo at 25° C. The resulting yellow oil was passed through a short column of SiO2 eluting with 3% TEA in hexanes to yield 1.82 g (7.97 mmol, 61%) of compound 1A as an orange oil.

Workup

  1. customthe volatiles were removed in vacuo at 25° C

Sources & evidence

ORD record
ord-93be66bbdeda4980b05cd5951053f235
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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