Iodine → 1-Iodo-3-triphenylmethoxy-trans-1-octene

HRID 225356

반응식

HRID 225356 반응식
[BH4-].[Na+].CC(=CC)C.B(F)(F)F.CCOCC.[C:17]1([C:23]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:24][CH:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:26]#[CH:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I:45]I>O1CCCC1.COCCOCCOC>[I:45]/[CH:27]=[CH:26]/[CH:25]([O:24][C:23]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

참가 물질

8

반응물 5

HCID 807IodineHCID 8000Boron trifluoride etherateHCID 105532-Methyl-2-buteneHCID 4311764Sodium borohydrideHCID 126753473-Triphenylmethoxy-1-octyne

생성물 1

HCID 201446361-Iodo-3-triphenylmethoxy-trans-1-octene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8150Diglyme용매

실험 절차

To a mixture of 0.650 g. (16.91 mmole) of sodium borohydride and 3.17 g. (45.2 mmoles) of 2-methyl-2-butene in 40 ml. of diglyme cooled to -5° C. under an inert atmosphere is added over 15 minutes 3.24 g. (22.6 mmoles) of boron trifluoride etherate and the resulting mixture is stirred at 0° C. for 2 hours. To this mixture is then added over 5 minutes 8.32 g. (22.6 mmoles) of 3-triphenylmethoxyl-1-octyne (Example 127) in 10 ml. diglyme, the cooling bath is removed, and the mixture is stirred at ambient temperature for 1.5 hours. The mixture is cooled to 0° C. and 6.0 g. of finely divided anhydrous trimethylamine oxide is added over 10 minutes. The cooling bath is removed and the mixture is stirred at ambient temperatures for 0.5 hour. The mixture is then poured into 200 ml. of 15 % sodium hydroxide solution, a solution of 16 g. (63 mmoles) of iodine in 20 ml. of tetrahydrofuran is added immediately, and the resulting mixture is stirred for 0.5 hour. The organic phase is separated and the aqueous phase is washed with ether. The combined organic phase and washings are decolorized with 5% sodium thiosulfate solution, washed with saturated brine, dried (Na2SO4), and evaporated. The residue is dry-columned chromatographed upon alumina using hexane as eluent and the title compound is isolated as an oil.

후처리

  1. additionTo a mixture of 0.650 g
  2. additionis added over 15 minutes 3.24 g
  3. additionTo this mixture is then added over 5 minutes 8.32 g
  4. customdiglyme, the cooling bath is removed
  5. temperatureThe mixture is cooled to 0° C.
  6. additionof finely divided anhydrous trimethylamine oxide is added over 10 minutes
  7. customThe cooling bath is removed
  8. stirringthe mixture is stirred at ambient temperatures for 0.5 hour
  9. additionThe mixture is then poured into 200 ml
  10. stirringthe resulting mixture is stirred for 0.5 hour
  11. customThe organic phase is separated
  12. washthe aqueous phase is washed with ether
  13. washwashed with saturated brine
  14. dry with materialdried (Na2SO4)
  15. customevaporated
  16. customThe residue is dry-columned chromatographed upon alumina

출처 및 근거

ORD 기록
ord-bf9def4ce6e34c1d8fd85a7b95356646
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04236027

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