Citric Acid → 1-[5-(Tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanol

HRID 2040044

반응식

HRID 2040044 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[O:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=1.[CH3:16][Mg]Cl.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CC(OC)(C)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[O:13][C:12]([CH:14]([OH:15])[CH3:16])=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 962WaterHCID 130977995-(Tetrahydro-pyran-2-yloxymethyl)-furan-2-carbaldehydeHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 668201851-[5-(Tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanol수율 95%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
1 °C

실험 절차

Crude 5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-carbaldehyde (171 g) was dissolved in THF (1 L) and cooled to 1° C. Methylmagnesium chloride (3 M in THF, 325 mL, 0.97 mol) was then added while keeping the internal temperature below 5° C. After the addition, the reaction mixture was stirred at rt for 1 h. Water (1 L), TBME (1 L) and 40% aq. citric acid (200 mL) were added, the layers separated and the org. layer washed with water (500 mL) and evaporated to dryness to give 174 g of crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanol (95% yield). Part of the crude material (96 g, 0.43 mol) was dissolved in CH2Cl2 (1 L) and treated with MnO2 (371 g, 4.26 mol) at rt. The reaction mixture was heated to 45° C. and stirred at this temperature for 24 h. The mixture was then filtered over celite and the filter cake washed with CH2Cl2. The filtrate was evaporated to dryness to give crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanone (89 g, 93%) as a yellow oil.

후처리

  1. customthe internal temperature below 5° C
  2. additionAfter the addition
  3. customthe layers separated
  4. washlayer washed with water (500 mL)
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-79cffd202044423b9f56460cec505797
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580831B2

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