Dimethylformamide → 6-Hydroxy-2-naphthaldehyde

HRID 374868

반응식

HRID 374868 반응식
[Li+].CCC[CH2-].Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]2.C([Li])(C)(C)C.CN(C)P(N(C)C)(N(C)C)=O.CN(C)[CH:36]=[O:37]>C1COCC1>[OH:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:36]=[O:37])[CH:16]=[CH:15]2

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 12679HexamethylphosphoramideHCID 271446-Bromo-2-naphthalenolHCID 61028n-Butyl lithiumHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 27641106-Hydroxy-2-naphthaldehyde수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Step a) N-Butyllithium (35.9 mL, 89.7 mmol) was added dropwise to a cold (-78° C.) solution of 6-bromo-2-naphthol (20.0 g, 89.7 mmol) in THF (200 mL). After stirring for 10 minutes, tertbutyllithium (52.76 mL, 89.7 mmol) was added dropwise. The mixture was stirred for 30 min at -78° C, and two hours at -20° C. Then, hexamethylphosphoramide (15.6 mL, 89.7 mmol) was added to the reaction mixture. After stirring for 20 minutes. N,N-dimethylformamide (6.94 mL, 89.7 mmol) was added dropwise. The mixture was allowed to come to room temperature, stirred for 1 hour, and quenched with aqueous ammonium chloride. The mixture was poured into water, acidified with 2N HCL and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexane/EtOAc 3/1 ), gave a yellow solid (12.5 g, 81% yield, m.p. 173°-174 ° C.).

후처리

  1. stirringThe mixture was stirred for 30 min at -78° C
  2. customtwo hours
  3. customat -20° C
  4. stirringAfter stirring for 20 minutes
  5. customto come to room temperature
  6. stirringstirred for 1 hour
  7. customquenched with aqueous ammonium chloride
  8. additionThe mixture was poured into water
  9. extractionextracted with EtOAc
  10. dry with materialThe organic extracts were dried over MgSO4
  11. customEvaporation and purification by flash chromatography (hexane/EtOAc 3/1 )

출처 및 근거

ORD 기록
ord-45a5ead73b5d4e6f824c9900e697d11b
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05482968

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