Sodium Methoxide → HCID 11367093, compound

HRID 985128Notes

Reaction equation

HRID 985128 reaction equation
C([O:4][C@H:5]1[C@@H:11]([O:12]C(=O)C)[CH2:10][O:9][CH:7]([OH:8])[C@@H:6]1[F:16])(=O)C.C[O-].[Na+]>CO>[F:16][C@@H:6]1[C@@H:5]([OH:4])[C@@H:11]([OH:12])[CH2:10][O:9][CH:7]1[OH:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11470372GlyTouCan:G81662TJ

Product 1

HCID 11367093HCID 11367093, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 17 (5.7 g, 24.1 mmol) in dry methanol (220 mL) was treated with 0.1 N NaOMe in methanol (114 mL, 11.4 mmol) and stirred for 1 hour at room temperature. The solution was then neutralized with DOWEX 50W X8-100, filtered and evaporated to afford 18 (3.7 g, 24 mmol, 100%) as a yellow syrup: 13C-NMR (D2O) δ 94.19 (C-1α, d, JC-1,F=23.0), 92.24 (C-2α, d, JC-2,F=179.6), 90.10 (C-1β, d, JC-1,F=20.3), 88.60 (C-2β, d, JC-2,F=182.3), 70.77 (C-3α, d, JC-3,F=18.2), 69.03 (C-4β, d, JC-4,F=8.0), 68.90 (C-4α, d, JC-4,F=10.2), 66.85 (C-3β, d, JC-3,F=18.2), 66.32 (C-5α), 62.21 (C-5β).

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-fbf79add1aa344e0b4ca5697d4150723
Source dataset
uspto-grants-2005_03
Patent number
US06870048B2

Reaction notes

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