Formaldehyde → HCID 18626562, compound

HRID 1859762Notes

Reaction equation

HRID 1859762 reaction equation
[CH:1]1[C:14]2[CH:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH2:25]=[O:26]>C1COCC1.CN1C(=O)N(C)CCC1>[OH:26][CH2:25][C:13]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 3

HCID 712Formaldehyde2×HCID 235688ethyl 9H-xanthene-9-carboxylateHCID 178418339Butyllithium

Product 1

HCID 18626562HCID 18626562, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
-50 °C

Procedure

A mixture of 1.5 g (5.9 mmol) of ethyl 9H-xanthene-9-carboxylate in 20 ml of THF and 1.6 ml of DMPU under an inert atmosphere is cooled to −50° C. 4 ml (6.4 mmol) of BuLi (1.6 M in hexane) are added dropwise to this medium with stirring, and the medium is then left stirring for 10 minutes at −40° C. After allowing the reaction medium to warm to 10° C., a flow of formaldehyde generated from 5.4 g (0.18 mol) of sublimed paraformaldehyde entrained by a stream of nitrogen is bubbled in. After stirring for 2 hours at room temperature, the suspension is dispersed in 50 ml of water. The reaction medium is then extracted twice with 100 ml of ether. The combined organic phases are dried over Na2SO4. After evaporation, the residual oil is chromatographed on silica. Eluent: CH2Cl2. 1.1 g of a yellow oil are obtained (yield: 68%).

Workup

  1. waitthe medium is then left
  2. stirringstirring for 10 minutes at −40° C
  3. temperatureto warm to 10° C.
  4. customis bubbled in
  5. stirringAfter stirring for 2 hours at room temperature
  6. additionthe suspension is dispersed in 50 ml of water
  7. extractionThe reaction medium is then extracted twice with 100 ml of ether
  8. dry with materialThe combined organic phases are dried over Na2SO4
  9. customAfter evaporation
  10. customthe residual oil is chromatographed on silica

Sources & evidence

ORD record
ord-efa3bfceeb1b4119ab06b2156f3e3855
Source dataset
uspto-grants-2003_03
Patent number
US06528538B1

Reaction notes

Loading…