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tert-Butanol → Docos-21-ynoic Acid. Tert.-Butyl Ester

HRID 2399983
ノート
印刷プレビュー

反応式

HRID 2399983 の反応式
[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][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][C:21]#[CH:22].CN(C1C=CC=CN=1)C.[C:34](O)([CH3:37])([CH3:36])[CH3:35].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.C(O)C>[C:1]([O:24][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][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][C:21]#[CH:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 54502951Docos-21-ynoic Acid

生成物 1

HCID 86749000Docos-21-ynoic Acid. Tert.-Butyl Ester収率 86.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 6212
Chloroform
溶媒

実験手順

The acid (32) (6.4 g, 0.019 mol) was dissolved in dry, ethanol free, chloroform (120 ml) at room temperature under nitrogen and sequentially treated with dimethylaminopyridine (2.55 g, 0.0209 mol), tert butanol (14.09 g, 0.19 mol), dimethylaminopyridine-trifluoroacetic acid complex (4.94 g, 0.0209 mol) and dicyclohexylcarbodiimide (4.31 g, 0.0209 mol). The resulting solution was stirred at room temperature overnight then filtered, the organic layer washed with 5% acetic acid in water, then dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel (50 g). Elution with 10% ether in petrol gave the title compound (33) as white crystals (6.45 g, 86%) mp 44°-45° C.

後処理

  1. customin dry
  2. filtrationthen filtered
  3. washthe organic layer washed with 5% acetic acid in water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (50 g)
  8. washElution with 10% ether in petrol

出典と根拠

ORDレコード
ord-855eab96cae946449702111060dc039e
出典データセット
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05451691

反応ノート

読み込み中…

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