Boron trifluoride → 10-(Hydroxymethyl)anthracene-9-carbaldehyde

HRID 2057559

반응식

HRID 2057559 반응식
[O:1]1[CH2:3][C:2]21[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:10]1([CH2:18][O:17]1)[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]2=1.B(F)(F)F.C(=O)(O)[O-].[Na+]>CCOCC>[OH:17][CH2:18][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:2]([CH:3]=[O:1])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2

참가 물질

5

반응물 3

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 3321211Dispiro(oxirane-2,9'(10'H)-anthracene-10',2''-oxirane)

생성물 1

HCID 376503610-(Hydroxymethyl)anthracene-9-carbaldehyde

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
-45 °C

실험 절차

To a solution of 500 mg. of the product of Example 1 in 50 ml. of anhydrous ether maintaining at -45° C. is added dropwise a solution of 0.060 ml. of boron trifluoride in 2.0 ml. of anhydrous ether. The reaction mixture is stirred at -45° C. for 10 minutes and then allowed to warm to -30° C. in 5 minutes. The reaction mixture is poured into a mixture of 20 ml. of cool saturated sodium bicarbonate solution and 30 ml. of ether. The ethereal solution is washed with an additional 20 ml. of saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and filtered. The ether is removed to provide a yellow solid. The solid is recrystallized from acetonitrile to give 259 mg. of the desired product as yellow crystals, mp. 182°-184° C.

후처리

  1. temperatureto warm to -30° C. in 5 minutes
  2. additionThe reaction mixture is poured into a mixture of 20 ml
  3. washThe ethereal solution is washed with an additional 20 ml
  4. dry with materialof saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe ether is removed
  7. customto provide a yellow solid
  8. customThe solid is recrystallized from acetonitrile
  9. customto give 259 mg

출처 및 근거

ORD 기록
ord-473f31cc4b244f95b7a217b5bc64ab36
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04211726

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