Oxygen → 6-Heptyn-1-ol

HRID 1160644노트

반응식

HRID 1160644 반응식
[OH:1][CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:9][CH2:10][CH2:11][C:12]#[C:13][CH2:14][CH2:15][CH3:16].[OH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[CH:24].O=O>N1C=CC=CC=1.CO.Cl[Cu]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8].[OH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:24]#[C:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][OH:17]

참가 물질

8

반응물 4

HCID 977OxygenHCID 846933-Heptyn-1-olHCID 5351112-Heptyn-1-olHCID 110078496-Heptyn-1-ol2회

생성물 2

HCID 110078496-Heptyn-1-olHCID 111278826,8-Tetradecadiyne-1,14-diol

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 22021344Pyridine methanol용매

실험 절차

HO(CH2)5C≡CH was prepared by the KAPA-promoted isomerization of HOCH2C≡C(CH2)3CH3 (prepared according to Millar, J. G.; Oehlschlager, A. C. J. Org. Chem. 1984, 49, 2332-2338) or HO(CH2)2C≡C(CH2)2CH3 (commercially available GFS Chemicals; Powell, Ohio). Oxidative coupling of HO(CH2)5C≡CH was carried out in a glass reaction vessel by dissolving 6.95 grams of HO(CH2)5C≡CH in pyridine/methanol (2.0 milliliters/6.2 milliliters) and adding 307 grams of CuCl followed by stirring in the presence of oxygen until all the staring material was consumed. The reaction mixture was worked up with diethyl ether and 4N HCl, the combined organic layers were dried over MgSO4, filtered and concentrated. Recrystallization of the residue from 1/1 hexanes/tert-butyl methyl ether to yield 5.35 grams of HO(CH2)5C≡C—C≡C(CH2)5OH as a pink solid.

후처리

  1. customprepared
  2. customwas consumed
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customRecrystallization of the residue from 1/1 hexanes/tert-butyl methyl ether

출처 및 근거

ORD 기록
ord-c6fa6497c8754c6aae419390de5f66d9
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816473B2

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