Triethylamine → HCID 54297662, compound

HRID 1738339Notes

Reaction equation

HRID 1738339 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C@@H:3]([OH:7])[CH2:4][C:5]#[CH:6].C(N(CC)CC)C.FC(F)(F)S(O[Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]([CH3:9])([CH3:8])[C@@H:3]([O:7][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:4][C:5]#[CH:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 54058176HCID 54058176, compound

Product 1

HCID 54297662HCID 54297662, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (S)-5,5-dimethyl-1-hexyn-4-ol (1.96 g 16 mmol), triethylamine (4.5 ml, 32 mmol) and dry dichloromethane (30 ml) was cooled to 0° C. under a nitrogen atmosphere. Triethylsilyl trifluoromethanesulphonate (5.4 ml, 24 mmol) was slowly added and the mixture stirred at 0° C. for a further 40 min. The mixture was treated with saturated sodium bicarbonate solution (60 ml) and the organic layer separated. The aqueous layer was extracted with dichloromethane (3×20 ml) and the combined dichloromethane extracts dried (MgSO4) and evaporated. The residue was purified by column chromatorgaphy (silica eluted with Petroleum ether 40-60°) to yield the title compound 3.55 g (95%).

Workup

  1. customthe organic layer separated
  2. extractionThe aqueous layer was extracted with dichloromethane (3×20 ml)
  3. dry with materialthe combined dichloromethane extracts dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatorgaphy (silica eluted with Petroleum ether 40-60°)

Sources & evidence

ORD record
ord-54dbc43218124fccba0b2e8b8b8e0039
Source dataset
uspto-grants-1999_10
Patent number
US05962659

Reaction notes

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