Acetic Acid → HCID 54236291, compound

HRID 582524Notes

Reaction equation

HRID 582524 reaction equation
C([O:8][CH2:9][CH:10]([C@H:12]1[CH2:16][O:15][C@@H:14]([CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:13]1)[OH:11])C1C=CC=CC=1.C[O-].[Na+].C(O)(=O)C>CO>[Si:19]([O:18][CH2:17][C@H:14]1[O:13][C@@H:12]([CH:10]([OH:11])[CH2:9][OH:8])[CH2:16][O:15]1)([C:32]([CH3:34])([CH3:35])[CH3:33])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 18649513HCID 18649513, compound

Product 1

HCID 54236291HCID 54236291, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (-)-(2R,4R)-4-(2-benzoxy-1-hydroxyethyl)-2-(t-butyldiphenylsilyloxy-methyl)-dioxolane (2.52 g, 5.0 mmole) in methanol (40 ml) was added a 0.078 M solution of sodium methoxide (7.3 ml) in methanol. The mixture stirred at room temperature for two hours. The mixture was neutralized with acetic acid and concentrated. The residue was then portioned between ethyl acetate and water, and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with a saturated NaHCO3 solution and then water, and then dried, evaporated, and purified by column chromatography over silica gel to yield 6 (1.9 g, 95%) as colorless oil: [α]25D-2° (C 0.25, MeOH); 1H NMR (DMSO-d6) δ 1.00 (s, 9H, t-Bu), 3.40-3.52 (m, 3H, CH2OH and CHOH), 3.64 (d, J=3.7 Hx, 2H, CH2O TBDPS), 3.82-3.95 (m, 3H, 4.5-H), 4.49 (t, J-5.3 Hz, 1H, pri OH, D2O exchangeable), 4.82 (d, J=5.1 Hz, 1H, sec OH, D2O exchangeable), 5.01 (t, J-3.7 Hz, 1H, 2-H), 7.36-7.71 (m, 1OH, Ar--H); Anal. Calcd for C22H33H30O5Si: C, 65.63; H, 7.53. Found: C, 65.72; H, 7.52.

Workup

  1. concentrationconcentrated
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated NaHCO3 solution
  4. dry with materialwater, and then dried
  5. customevaporated
  6. custompurified by column chromatography over silica gel

Sources & evidence

ORD record
ord-12ea0b1e41614deda8a28aabd635fcfa
Source dataset
uspto-grants-1999_07
Patent number
US05925643

Reaction notes

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