Tetrahydrofuran → HCID 15592210, compound

HRID 615929Notes

Reaction equation

HRID 615929 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=1.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:22]([OH:21])[CH2:23][CH2:24][CH2:25][CH2:19][CH2:18][CH2:17][CH2:16][CH2:16][CH2:17][CH2:18][CH2:19][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 15592209HCID 15592209, compoundHCID 178418339Butyllithium

Product 1

HCID 15592210HCID 15592210, compound

Procedure

A solution of the product of Example 4 (4 mmoles) in tetrahydrofuran (150 ml) was cooled to ca.-75° C. under an atmosphere of argon. n-Butyllithium (2 ml, 2.04 M in hexane) was added by syringe over 15 min. while maintaining the reaction temperature below -70° C., and the solution then stirred for 3.5 hours. A cold solution (ca.-8° C.) of octadecyl aldehyde (4 mmoles) in tetrahydrofuran (100 ml) was canulated by syringe to the above solution over 25 min., keeping the temperature below -60° C. The reaction temperature rose to 25° C. during the next 2 hours, after which the reaction was quenched with water (10 ml) and stirred overnight. After removing the tetrahydrofuran under a nitrogen stream, water (75 ml) was added and the product extracted into ethyl acetate. The combined extract was dried over sodium sulfate, filtered and stripped under reduced pressure to give 1.7 g of an oil. The product was purified by chromatography on silica gel to give 0.85 g of the title compound, m.p. ca.74°-78° C.

Workup

  1. custom-75° C.
  2. temperaturewhile maintaining the reaction temperature below -70° C.
  3. customthe temperature below -60° C
  4. customrose to 25° C. during the next 2 hours
  5. customafter which the reaction was quenched with water (10 ml)
  6. stirringstirred overnight
  7. customAfter removing the tetrahydrofuran under a nitrogen stream, water (75 ml)
  8. additionwas added
  9. extractionthe product extracted into ethyl acetate
  10. extractionThe combined extract
  11. dry with materialwas dried over sodium sulfate
  12. filtrationfiltered

Sources & evidence

ORD record
ord-69916678aca64d2a97666ee06b86e3dc
Source dataset
uspto-grants-1985_02
Patent number
US04501895

Reaction notes

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