Acetic Acid → HCID 86752988, compound

HRID 365773Notes

Reaction equation

HRID 365773 reaction equation
[Si]([O:18][CH2:19][C@@H:20]1[CH2:24][O:23][C@@H:22]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[S:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1>[CH2:28]([O:27][P:25]([O:30][CH2:31][CH3:32])([C@H:22]1[S:21][C@H:20]([CH2:19][OH:18])[CH2:24][O:23]1)=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131720783HCID 131720783, compound

Product 1

HCID 86752988HCID 86752988, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cis and trans 4-(t-butyldiphenylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-oxathiolane (example 42) (5.00 g, 10.07 mmol) in tetrahydrofurane (300 mL) was added tetrabutylammonium fluoride (15.0 mL, 15.0 mmol, 1.5 eq) at room temperature. The solution was stirred at room temperature for 45 min and acetic acid was added (850 μL) followed by evaporation under reduced pressure. The crude material was purified by flash chromatography with ethyl acetate to give the pure compound (2.47 g) in 96% yield.

Workup

  1. customfollowed by evaporation under reduced pressure
  2. customThe crude material was purified by flash chromatography with ethyl acetate

Sources & evidence

ORD record
ord-e088f71d586d4cf0bce83a5b1cfb5f6a
Source dataset
uspto-grants-2000_10
Patent number
US06127540

Reaction notes

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