Formaldehyde → HCID 25129447, compound

HRID 1889123Notes

Reaction equation

HRID 1889123 reaction equation
[Si:1]([O:18][C@@H:19]([CH2:22][CH2:23][CH2:24][OH:25])[CH2:20][OH:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.B(F)(F)F.[CH3:32]COCC>CCOC(C)=O>[Si:1]([O:18][C@H:19]1[CH2:22][CH2:23][CH2:24][O:25][CH2:32][O:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8000Boron trifluoride etherateHCID 25133549HCID 25133549, compound

Product 1

HCID 25129447HCID 25129447, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 6a (0.55 g, 1.5 mmol) and paraformaldehyde (46 mg, 1.5 mmol) in EtOAc (30 mL), boron trifluoride etherate (195 μL, 1.5 mmol) was added and the resulting mixture was stirred at 23° C. for 4 h. The organic phase was washed with a saturated solution of NaHCO3, dried (Na2SO4) and the solvent was removed. The residue was purified by flash-chromatography (1:4 EtOAc/Hex) to afford 0.29 g (51%) of 7a as a colourless oil: [α]D20=−8.7 (c 1.9, CHCl3); 1H NMR (CDCl3) δ 7.67-7.63 (m, 4H), 7.45-7.34 (m, 6H), 4.69 (d, J=6.2 Hz, 1H), 4.45 (d, J=6.2 Hz, 1H), 4.03-3.95 (m, 1H), 3.70-3.61 (m, 1H), 3.59-3.48 (m, 3H), 1.93-1.80 (m, 1H), 1.77-1.61 (m, 2H), 1.47-1.34 (m, 1H), 1.12 (s, 9H); 13C NMR (CDCl3) δ 135.7, 134.2, 129.5, 127.5, 95.6, 72.2, 71.9, 69.0, 33.2, 27.0, 26.7, 19.2.

Workup

  1. additionwas added
  2. washThe organic phase was washed with a saturated solution of NaHCO3
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed
  5. customThe residue was purified by flash-chromatography (1:4 EtOAc/Hex)

Sources & evidence

ORD record
ord-1c3ec170f4a64042b46a37d164b9b79f
Source dataset
uspto-grants-2013_08
Patent number
US08501961B2

Reaction notes

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