Dimethyl Sulfoxide → 7-Methylpentadecene-1-ol

HRID 366996

반응식

HRID 366996 반응식
[H-].[Na+].[Br-].[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CS(C)=O.[CH3:34][C:35](=O)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>O>[CH3:34][CH:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][OH:4]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 127412-DecanoneHCID 24758Sodium hydrideHCID 2784664Phosphonium, (6-hydroxyhexyl)triphenyl-, bromide

생성물 1

HCID 734445857-Methylpentadecene-1-ol수율 49.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g).

후처리

  1. customInto a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet
  2. customThe mineral oil is removed
  3. washby washing with hexanes
  4. additionAnhydrous dimethyl sulfoxide (500 ml) is added to the flask
  5. temperatureThe reaction mixture is cooled to room temperature
  6. additionfollowed by addition of 1 L of anhydrous tetrahydrofuran
  7. additionslowly added to the reaction mixture thru the dropping funnel
  8. customthe reaction at 25-30° C
  9. additionis slowly added thru a dropping funnel
  10. customReaction
  11. temperaturecooling
  12. temperatureto maintain 25-30° C
  13. additionand then poured into a separatory funnel
  14. stirringAfter shaking the oil phase (top)
  15. customto separate out
  16. customthe water phase is removed
  17. extractionThe extractions of the oil phase
  18. customThe organic phase is collected
  19. distillationvacuum distilled
  20. custompurified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase)

출처 및 근거

ORD 기록
ord-911b87097d6e481c999e15618f52c2a5
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133222

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