1-Pentyne → 1-Chlorooct-4-yn-3-ol

HRID 1659022노트

반응식

HRID 1659022 반응식
C([Li])CCC.[CH:6]#[C:7][CH2:8][CH2:9][CH3:10].Cl[CH:12]([CH3:15])[CH:13]=[O:14].[Cl-:16].[NH4+]>CCCCCC>[Cl:16][CH2:15][CH2:12][CH:13]([OH:14])[C:6]#[C:7][CH2:8][CH2:9][CH3:10]

참가 물질

6

반응물 4

HCID 123091-PentyneHCID 25517Ammonium ChlorideHCID 1354402-ChloropropanalHCID 178418339Butyllithium

생성물 1

HCID 204655481-Chlorooct-4-yn-3-ol

시약·촉매·용매 1

HCID 8058Hexane용매2회

실험 절차

To 68 ml. of 1.6M butyllithium in hexane at -50°C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10°C. and treated with 11 g. of freshly prepared β -chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15°C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66°C. at 0.3 nm.; λ max. 2.95 (--OH) and 4.55 μ (-C≡C-); vapor phase chromatography shows one peak.

후처리

  1. additionThe resulting white sludge is diluted with 20 ml
  2. custombrought to 10°C.
  3. additiontreated with 11 g
  4. temperatureis maintained at 10°-15°C
  5. stirringto stir at ambient temperature for 18 hours
  6. customThe organic phase is separated
  7. washwashed
  8. additionwith dilute hydrochloric solution
  9. dry with materialdried with anhydrous magnesium sulfate
  10. distillationDistillation
  11. customgives 5.1 g

출처 및 근거

ORD 기록
ord-a88cfad6576149f4a081ac99b2c25ef8
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03966773

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