Sodium Methoxide → HCID 118151937, compound

HRID 1506967Notes

Reaction equation

HRID 1506967 reaction equation
C([O:7][CH2:8][CH2:9][C@H:10]1[C@H:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:13][C:12]([CH2:24][CH3:25])([CH2:22][CH3:23])[O:11]1)(=O)C(C)(C)C.C[O-].[Na+]>CO.CCOC(C)=O>[CH2:15]([C@@H:14]1[O:13][C:12]([CH2:22][CH3:23])([CH2:24][CH3:25])[O:11][C@H:10]1[CH2:9][CH2:8][OH:7])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 90026583HCID 90026583, compound

Product 1

HCID 118151937HCID 118151937, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of (2-((4S,5S)-5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl pivalate (Preparation example 246, 1.0 g, 2.87 mmol) in MeOH (10 mL) was added NaOMe (0.47 g, 8.61 mmol) and then warm to 45° C. The mixture was stirred for 14 h. The resulting mixture was diluted with EtOAc, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude compound was purified by a silica gel column to produce the title compound (0.7 g, 80˜95%);

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-2c444fce8af04a0d8220f101705c7146
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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