Formaldehyde → HCID 20364904, compound

HRID 1889130Notes

Reaction equation

HRID 1889130 reaction equation
[CH2:1]([O:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.B(F)(F)F.[CH3:20]COCC>CCOC(C)=O>[CH2:1]([O:8][CH:9]1[CH2:10][O:11][CH2:20][O:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8000Boron trifluoride etherateHCID 2035672-(Phenylmethoxy)-1,3-propanediol

Product 1

HCID 20364904HCID 20364904, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 17 (100 mg, 0.55 mmol) and paraformaldehyde (17 mg, 0.55 mmol) in EtOAc (10 mL), boron trifluoride etherate (70 μL, 0.55 mmol) was added and the reaction mixture was stirred at 23° C. for 4 h. The organic phase was washed with a saturated solution of NaHCO3, dried and the solvent was removed. The residue was purified by flash-chromatography eluting with a 1:4 mixture of EtOAc and hexanes to afford 84 mg (78%) of O-benzyl-1,3-dioxan-5-ol as a colourless oil. The above compound was dissolved in EtOAc (3 mL), Pd/C was added and the resulting suspension was stirred at rt under a hydrogen atmosphere. After 12 h, the catalyst was filtered off, the filtrate was evaporated in vacuo and the residue (39 mg, 100%) was used in the next step without further purification: 1H NMR (CDCl3) δ 4.93 (d, J=6.3 Hz, 1H), 4.76 (d, J=6.3 Hz, 1H), 3.94-3.84 (m, 4H), 3.64-3.61 (m, 1H), 2.78 (bs, 1H). 13C NMR (CDCl3) δ 94.0, 71.7, 64.1.

Workup

  1. additionwas added
  2. washThe organic phase was washed with a saturated solution of NaHCO3
  3. customdried
  4. customthe solvent was removed
  5. customThe residue was purified by flash-chromatography
  6. washeluting with a 1:4 mixture of EtOAc and hexanes

Sources & evidence

ORD record
ord-5e20ef3ecea24dd8890fa26cb8a3d2eb
Source dataset
uspto-grants-2013_08
Patent number
US08501961B2

Reaction notes

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