Formaldehyde → HCID 86729343, compound

HRID 1474598Notes

Reaction equation

HRID 1474598 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:31][CH3:32])[O:13][C@H:12]([CH:14]=[O:15])[C@@H:11]([O:16][Si](C)(C)C)[C@H:10]([O:21][Si](C)(C)C)[C@H:9]2[O:26][Si](C)(C)C)=[CH:4][C:3]=1[CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C=O.C[CH2:44][O-:45].[Na+].S(=O)(=O)(O)[O-].[Na+]>CCO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([O:31][CH3:32])[C@H:9]([OH:26])[C@@H:10]([OH:21])[C@H:11]([OH:16])[C:12]([CH2:44][OH:45])([CH2:14][OH:15])[O:13]2)=[CH:4][C:3]=1[CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516919Sodium BisulfateHCID 2723922Sodium ethoxideHCID 86729341HCID 86729341, compound

Product 1

HCID 86729343HCID 86729343, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (2S,3R,4S,5R,6S)-6-(4-chloro-3-(phenoxymethyl)phenyl)-6-methoxy-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-carbaldehyde (22.9 g, 36.7 mmol) in EtOH (92 mL) under nitrogen atmosphere, was added para-formaldehyde (33.0 g, 1.1 mol) at 55° C. followed by addition of 21% NaOEt in ethanol (23.12 g NaOEt/110 mL EtOH). The reaction mixture was heated at 55° C. overnight. After the completion of the reaction as confirmed by TLC, ethanol was evaporated. The crude compound was extracted with ethyl acetate (700 mL) followed by washing with sodium bisulphate solution (68.67 g, 660.6 mmol) in water (458.7 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford crude compound, which was purified by column chromatography (silica gel, 6:4 MeOH:DCM) to obtain the compound as a white solid (12 g).

Workup

  1. customAfter the completion of the reaction
  2. customwas evaporated
  3. extractionThe crude compound was extracted with ethyl acetate (700 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto afford crude compound, which
  8. customwas purified by column chromatography (silica gel, 6:4 MeOH:DCM)

Sources & evidence

ORD record
ord-506fe3c36c9f46129e269a6663cb8b95
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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