Formaldehyde → HCID 59707354, compound

HRID 1422871Notes

Reaction equation

HRID 1422871 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Mg]Br)C.C1(C)C=CC=CC=1.[CH2:29]=[O:30]>C1COCC1.C(N(CC)CC)C.C(OCC)(=O)C.O>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:29]=[O:30])=[C:13]([OH:17])[CH:12]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 1140TolueneHCID 21933797HCID 21933797, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 59707354HCID 59707354, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1) (538 mg, 2.13 mmol) in THF (20 ml) and triethylamine (3 ml) cooled in an ice bath was added ethyl magnesium bromide (2.13 mL of a 1M solution, 2.13 mmol). The reaction was allowed to warm to room temperature and stirred for a total duration of 1 h. Solvent was removed under reduced pressure then toluene (50 ml) was added which was subsequently removed under reduced pressure. This procedure was repeated two times. After the third addition of toluene, paraformaldehyde (160 mg, 5.32 mmol) was added and the reaction was heated to reflux for 18 h. After cooling to room temperature, water (100 mL) and ethyl acetate (100 mL) were added; the organic layer was separated and washed with water (2×100 mL), dried over MgSO4, filtered and evaporated to dryness under reduced pressure to produce the crude product as a yellow oil. This crude product was purified by silcagel column chromatography, eluting with a gradient from 10%-50% ethyl acetate in hexane producing the final product as a yellow oil (100 mg, 17%).

Workup

  1. customSolvent was removed under reduced pressure
  2. additiontoluene (50 ml) was added which
  3. customwas subsequently removed under reduced pressure
  4. additionwas added
  5. temperaturethe reaction was heated
  6. temperatureto reflux for 18 h
  7. temperatureAfter cooling to room temperature
  8. customthe organic layer was separated
  9. washwashed with water (2×100 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cabf1fc752a84029ae6213d0158e5335
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

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