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Hydrochloric Acid → Methyl 5-tert-butylfuran-2-carboxylate

HRID 537749
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HRID 537749 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10]([O:12][CH3:13])=[O:11].[C:14](Br)([CH3:17])([CH3:16])[CH3:15].Cl>C(=S)=S>[C:14]([C:9]1[O:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=1)([CH3:17])([CH3:16])[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10485t-Butyl bromideHCID 11902Methyl 2-furoateHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 250082Methyl 5-tert-butylfuran-2-carboxylate

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

AlCl3 (25.4 g, 190 mmol) is added batchwise to methyl furan-2-carboxylate (20.0 g, 159 mmol) and tert.-butylbromide (21.4 mL, 190 mmol) in CS2 (200 mL) while cooling with ice and the mixture is stirred for 6 h at RT. The reaction mixture is poured onto ice water, mixed with conc. hydrochloric acid (25 mL) and stirred for 10 min. Then the aqueous phase is extracted 2× with 200 mL EA. The combined organic phase is dried on Na2SO4, filtered and evaporated down using the rotary evaporator. The methyl 5-tert.-butyl-furan-2-carboxylate thus obtained is used further without any additional purification steps.

후처리

  1. temperaturewhile cooling with ice
  2. additionThe reaction mixture is poured onto ice water
  3. stirringstirred for 10 min
  4. extractionThen the aqueous phase is extracted 2× with 200 mL EA
  5. customThe combined organic phase is dried on Na2SO4
  6. filtrationfiltered
  7. customevaporated down
  8. customthe rotary evaporator

출처 및 근거

ORD 기록
ord-2db3cf5d459d43328f9035965ebf1810
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865703B2

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