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

HRID 2399983
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인쇄 미리보기

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HRID 2399983 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 6212
Chloroform
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-855eab96cae946449702111060dc039e
출처 데이터셋
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05451691

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