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Hydrochloric Acid → 2-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid

HRID 1517535
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인쇄 미리보기

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HRID 1517535 반응식
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:5]=1[C:16]1[C:17]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:18][CH:19]=[CH:20][CH:21]=1.C1COCC1.[OH-].[Na+].Cl>CO.O>[CH2:23]([O:22][C:17]1[C:16]([C:5]2[CH:6]=[C:7]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:8]([O:10][CH3:11])=[CH:9][C:4]=2[C:3]([OH:30])=[O:2])=[CH:21][CH:20]=[CH:19][N:18]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 673789942-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid methyl ester

생성물 1

HCID 673744112-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid수율 97%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

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온도
70 °C

실험 절차

step 3—To a suspension of 66 (960 mg, 2.36 mmol) in MeOH (15 mL), H2O (10 mL), and THF (10 mL) was added NaOH (1.00 g, 23.6 mmol). The reaction mixture was heated at 70° C. overnight and gradually became homogeneous. The mixture was cooled to 0° C., acidified to pH 3 with 1.0 M aq HCl and thrice extracted with EtOAc. The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford 895 mg (97%) of 2-(2-benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid (68) as a beige solid.

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-897d4275b64940e5beef43f4bd3e5eb1
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08232271B2

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