Carbon Dioxide → HCID 13416643, compound

HRID 2309785Notes

Reaction equation

HRID 2309785 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([Li])(CC)C.[C:15](=[O:17])=[O:16].Cl>C1COCC1.CCCCCC>[OH:6][CH:5]1[C:4]2[C:3](=[C:2]([F:1])[CH:9]=[CH:8][CH:7]=2)[C:15](=[O:16])[O:17]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 680093-FluorobenzaldehydeHCID 178418400CID 53628100

Product 1

HCID 13416643HCID 13416643, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a -70° C. solution of the dimethylacetal of 3-fluorobenzaldehyde (5.3 g, 31 mmol) in THF (35 ml) was added dropwise sec-butyllithium (22.2 ml of a 1.4 M solution in hexane), and the red solution was stirred for 0.5 h. The solution was saturated with CO2 for 5 min with tne red color dissipating to yield a light yellow solution. After 10 min the reaction was allowed to warm to room temperature, and after 30 min HCl (3.5 ml) was added. After concentration the solution was made basic with 5% KOH (25 ml), the neutral material extracted with Et2O (2×40 ml), the base layer acidified to pH 1 witn HCl, and the product extracted with EtOAc (2×75 ml). Work up as usual afforded 4.5 g (86%) of the title compound, mp 11°-119°, suitable for use in the next step. Recrystallization of this material from EtOAc/PE gave analytically pure material: mp 126°-127° C.; IR 3400 (br s), 1740-1760 (structured s), 1630 (m), 1485 (m), 1300 (m), 1085 (s), 910 (m), 760 (m); 1H NMR 7.8-7.1 (highly structured m, 3 H), 6.60 (br s, 1H); exact mass calcd for C8H5O3F m/e 168.0227, obsd 168.0226.

Workup

  1. customto yield a light yellow solution
  2. waitAfter 10 min the reaction was allowed
  3. concentrationAfter concentration the solution
  4. extractionthe neutral material extracted with Et2O (2×40 ml)
  5. extractionthe product extracted with EtOAc (2×75 ml)

Sources & evidence

ORD record
ord-a1af4293b8814c4ebf3b57a0dd60c815
Source dataset
uspto-grants-1987_09
Patent number
US04697005

Reaction notes

Loading…