Propargyl alcohol → Nonadec-2-yn-1-ol

HRID 248149

反応式

HRID 248149 の反応式
[CH2:1]([OH:4])[C:2]#[CH:3].[Li].[CH2:6](Br)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O1CCCC1.N>[CH2:1]([OH:4])[C:2]#[C:3][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH3:6]

参加物

6

反応物 3

HCID 7859Propargyl alcoholHCID 82131-BromohexadecaneHCID 3028194Lithium

生成物 1

HCID 10967930Nonadec-2-yn-1-ol

試薬・触媒・溶媒 2

HCID 222Ammonia溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 56.1 g of propargyl alcohol in 100 ml of tetrahydrofuran and 15.6 g of lithium in 1 liter of ammonia containing a trace of ferric chloride is stirred for 1 hour. A 76.4 ml portion of hexadecyl bromide is added and the mixture refluxed for 8 hours then evaporated. The residue is dissolved in ether and washed with 10% hydrochloric acid, dried and purified by flash chromatography, to give 47.4 g of the desired compound as white platelets, mp. 60° C.

後処理

  1. temperaturethe mixture refluxed for 8 hours
  2. customthen evaporated
  3. dissolutionThe residue is dissolved in ether
  4. washwashed with 10% hydrochloric acid
  5. customdried
  6. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-03ad03efdbea4d5a919894b5736fd45f
出典データセット
uspto-grants-1993_05
特許番号
US05208223

関連ノート

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