Borane;tetrahydrofuran → 2-(Hydroxymethyl)-5-(methylsulfonyl)phenol

HRID 452447노트

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HRID 452447 반응식
[OH:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].O1CCCC1.B>C1COCC1>[OH:5][CH2:4][C:3]1[CH:7]=[CH:8][C:9]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:10][C:2]=1[OH:1]

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 184615502-Hydroxy-4-(methylsulfonyl)benzoic acid

생성물 1

HCID 668871582-(Hydroxymethyl)-5-(methylsulfonyl)phenol수율 98.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

2-hydroxy-4-(methylsulfonyl)benzoic acid (3.59 g, 16.6 mmol) was dissolved in dry THF (100 ml) under a blanket of nitrogen. The solution was cooled down to 0° C. and 1.0 M borane tetrahydrofuran complex (61.4 ml, 61.4 mmol) was slowly added. After completed addition the reaction mixture was brought to ambient temperature and stirred for 17 h. Then it was cooled once more to 0° C. and carefully quenched with water, acidified with aqueous HCl (5%) and finally extracted several times with EtOAc. The combined organic phases were dried (Na2SO4), filtered and evaporated to dryness. Since 50% of the starting material remained the reaction was done once more with THF (250 ml) and 1.0 M borane tetrahydrofurane (50 ml, 50 mmol). Same workup as before but prior to extraction the pH was adjusted to 7. The organic phase was dried (Na2SO4), filtered and evaporated under reduced pressure to give a white powder (3.3 g). 1H-NMR (400 MHz, MeOH): δ 7.6 (1H, d, J 8 Hz), δ 7.39 (1H, d, J 8 Hz), δ 7.28 (1H, s), δ 4.69 (2H, s), δ 3.06 (3H, s).

후처리

  1. addition1.0 M borane tetrahydrofuran complex (61.4 ml, 61.4 mmol) was slowly added
  2. additionaddition the reaction mixture
  3. customwas brought to ambient temperature
  4. temperatureThen it was cooled once more to 0° C.
  5. customcarefully quenched with water
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to dryness
  9. extractionSame workup as before but prior to extraction the pH
  10. dry with materialThe organic phase was dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-4bea8434fb2b4b68a30d5acecda79eb2
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492372B2

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