Pyridine → 3-Triphenylmethoxy-1-octyne

HRID 225355

반응식

HRID 225355 반응식
[CH:1]#[C:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10]1([C:16](Br)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1.[K+].[Br-]>O>[C:10]1([C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:2]#[CH:1])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 11692BromotriphenylmethaneHCID 131661-Octyn-3-olHCID 253877Potassium Bromide

생성물 1

HCID 126753473-Triphenylmethoxy-1-octyne

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1.26 g. (10.0 mmoles) of 1-octyn-3-ol, 4.85 g. (15.0 mmoles) of triphenylmethyl bromide, and 50 ml. of dry pyridine is heated at 95° C. for 60 minutes with occasional swirling. The solution is cooled, treated with water, and extracted with ether. The extract is washed successively with water and saturated sodium chloride, dried over magnesium sulfate, and concentrated. The crude product is purified by chromatography on Florisil and recrystallization from petroleum ether to give white crystals, m.p. 65°-66° C. λ max. (KBr) 3280 (acetylenic hydrogen), 1605, 1030, and 702 cm-1 (triphenylmethoxy group) .

후처리

  1. additionA mixture of 1.26 g
  2. temperatureThe solution is cooled
  3. extractionextracted with ether
  4. washThe extract is washed successively with water and saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by chromatography on Florisil and recrystallization from petroleum ether
  8. customto give white crystals, m.p. 65°-66° C. λ max

출처 및 근거

ORD 기록
ord-a0d9e404f94e42e6a0d8bd08988eb914
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04236027

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