Acetic Acid → HCID 86752988, compound

HRID 481714Notes

Reaction equation

HRID 481714 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. 1H NMR (300 MHz, CDCl3) δ: 1.36 (2t, 6H, J=7.1 Hz, CH3), 3.20 (m, 0.33H, CHAHBO for cis), 3.64 (m, 1.33H, CH2O for trans), 3.75 (m, 1H, OH and 0.33H, CHAHBO for cis), 3.95 (dd, 0.33H, J=6.1 Hz, 9.9 Hz, CHAHBO for cis), 4.23 (m, 4H, CH2 ; 1H H-4; 0.66H, CHAHBO for trans), 4.33 (dd, 0.66H, J=7.6 Hz, 9.9 Hz, CHAHBO for trans), 4.49 (dd, 0.33H, J=3.5 Hz, 9.9 Hz, CHAHBO for cis), 5.23 (d, 0.33H, 2JHP =9.9 Hz, H-2 for cis), 5.33 (d, 0.66H, 2JHP =9.3 Hz, H-2 for trans).

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-d7a294fc1e8442feaaa13140d629d483
Source dataset
uspto-grants-1998_08
Patent number
US05789394

Reaction notes

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