Acetic Acid → HCID 69799303, compound

HRID 1823210Notes

Reaction equation

HRID 1823210 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13](C2C=CC=CC=2)(C2C=CC=CC=2)[O:14][SiH2]C(C)(C)C)[CH2:11][C@@H:10]([CH2:32][CH3:33])[C:9]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][OH:14])[CH2:11][C@@H:10]([CH2:32][CH3:33])[C:9]1=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131725727HCID 131725727, compound

Product 1

HCID 69799303HCID 69799303, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound obtained from step A (5.2 g, 10.8 mmol) in THF (20 mL) and acetic acid (1.36 mL, 2.2 equiv.) at 0° C. was added TBAF (1.0 M in THF, 17.8 mL, 1.65 equiv). The mixture was stirred at rt for 2.0 h. It was then diluted with ethyl acetate and washed with 5% KHSO4 and brine. Evaporation of solvent and a column chromatography (EtOAc: hexane=1:1) gave the desired product as viscous oil (yield, 95%). 1HNMR (400 MHz, CDCl3) δ 4.11 (m, 1 H), 3.78 (dd, 2 H), 2.63 (m, 1 H), 2.15 (dd, 1 H), 1.99 (m, 1 H), 1.82 (m, 1 H), 1.55 (s, 9 H), 1.54 (m, 1 H), 0.97 (t, 3 H).

Workup

  1. washwashed with 5% KHSO4 and brine
  2. customEvaporation of solvent

Sources & evidence

ORD record
ord-17864d0c8e0b4599a4deda21d5d115b8
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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