Acetic Acid → HCID 86745125, compound

HRID 344825Notes

Reaction equation

HRID 344825 reaction equation
[CH3:1][C@H:2]1[CH:11]=[CH:10][C:9]2[C@H:4]([C@@H:5]([O:13][C:14](=[O:19])[C@@H:15]([CH3:18])[CH2:16][CH3:17])[CH2:6][C@@H:7]([CH3:12])[CH:8]=2)[C@H:3]1[CH2:20][CH2:21][C:22](=[O:38])[CH2:23][C@@H:24]([O:30][Si](C(C)(C)C)(C)C)[CH2:25][C:26]([O:28][CH3:29])=[O:27].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>O1CCCC1>[CH3:1][C@H:2]1[CH:11]=[CH:10][C:9]2[C@H:4]([C@@H:5]([O:13][C:14](=[O:19])[C@@H:15]([CH3:18])[CH2:16][CH3:17])[CH2:6][C@@H:7]([CH3:12])[CH:8]=2)[C@H:3]1[CH2:20][CH2:21][C:22](=[O:38])[CH2:23][C@@H:24]([OH:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 70424237HCID 70424237, compound

Product 1

HCID 86745125HCID 86745125, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The silyl ether from Step C (230 mg, 0.00024 mol) was dissolved in 5 ml of tetrahydrofuran (THF) and treated with 54 μl, (0.057 g, 0.00095 mol) of acetic acid and 710 μl (1M in THF, 0.00071 mol) of tetrabutylammonium fluoride (Bu4N F) and the mixture was stirred overnight at room temperature. Another 57 μl of acetic acid and 710 μl of Bu4N F were added and stirring was continued an additional 24 hours. The mixture was poured into 100 ml of ether and washed with 1×5 ml of 1N hydrochloric acid, 1×10 ml of saturated aqueous sodium bicarbonate and 2×10 ml of brine and dried (MgS04) Concentration to dryness gave 120 mg of an oil. The oil was chromatographed on a "Still" column of silica gel (1.5×17.7 cm, 230-400 mesh) by elution with 5% acetone in methylene chloride (v/v) collecting 5 ml fractions. Fractions 12-20 containing the product were combined and concentrated to dryness to give 53 mg of solid (m.p. 64°-66° C.). Recrystallization of a sample from hexane gave material with m.p. 67°-68° C.

Workup

  1. stirringstirring
  2. waitwas continued an additional 24 hours
  3. washwashed with 1×5 ml of 1N hydrochloric acid, 1×10 ml of saturated aqueous sodium bicarbonate and 2×10 ml of brine
  4. customdried
  5. concentration(MgS04) Concentration to dryness

Sources & evidence

ORD record
ord-092640fee2f6439288c492058df2fa3e
Source dataset
uspto-grants-1991_10
Patent number
US05053525

Reaction notes

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