Formaldehyde → HCID 21253832, compound

HRID 2395089Notes

Reaction equation

HRID 2395089 reaction equation
C([Li])CCC.[N:6]([CH2:9][CH2:10][C:11]#[CH:12])=[N+:7]=[N-:8].[CH2:13]=[O:14].[Cl-].[NH4+]>C1COCC1>[N:6]([CH2:9][CH2:10][C:11]#[C:12][CH2:13][OH:14])=[N+:7]=[N-:8]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 13816332HCID 13816332, compoundHCID 178418339Butyllithium

Product 1

HCID 21253832HCID 21253832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (1.6M in hexane, 18.8 mmol, 11.7 ml) was added dropwise at -78° C. to a solution of 4-azido-1-butyne II-32 (1.28 g, 17.3 mmol) in THF (35 ml). After stirring the resulting green solution for 1 h, paraformaldehyde was added in one portion, the solution was stirred for 5 min, and then warmed to room temperature for 2 h (an orange suspension gradually formed). The reaction mixture was poured into saturated aqueous ammonium chloride (100 ml) and extracted with ether (3×50 ml). The combined extracts were washed with brine (50 ml), dried over sodium sulphate and evaporated to give a yellow oil. This was purified by flash chromatography eluting with pentane/ether 1:1 to afford the title compound II-33 as a pale yellow oil (930 mg, 70.7%): IR (CHCl3) 3600 (m), 3000 (m), 2940 (m), 2880 (m), 2100 (s), 1550 (w), 1380 (m), 1270 (m), 1220 (br), 1140 (m), 1000 (s) cm-1 ; 1H NMR (500 MHz, CDCl3) δ4.24-4.22 (m, 2 H), 3.37 (t, J=6.8 Hz, 2 H), 2.51-2.48 (m, 2 H), 1.84 (t, J=6.0 Hz, 1 H); 13C NMR (62.9 MHz, CDCl3) δ77.42, 70.47, 49.68, 19.45.

Workup

  1. stirringthe solution was stirred for 5 min
  2. customgradually formed)
  3. extractionextracted with ether (3×50 ml)
  4. washThe combined extracts were washed with brine (50 ml)
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customto give a yellow oil
  8. customThis was purified by flash chromatography
  9. washeluting with pentane/ether 1:1

Sources & evidence

ORD record
ord-b6b8ca4691d849d6a0fa4b62644f9cc6
Source dataset
uspto-grants-1998_09
Patent number
US05811512

Reaction notes

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