Acetic Acid → (S)-2-Bromo-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester

HRID 464567노트

반응식

HRID 464567 반응식
[Br:1][C@@H:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].[C:15]1([C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N+]=[N-])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C>CC(C)=O>[Br:1][C@@H:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:4]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 12961659Propanoic acid, 2-bromo-3-(phenylmethoxy)-, (S)-

생성물 1

HCID 13505683(S)-2-Bromo-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester수율 51%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of (S)-2-bromo-3-(phenylmethoxy)propanoic acid (7.63 g, 29.4 mmol) in acetone (30 ml) was added solid diphenyldiazomethane (5.81 g, 29.9 mmol) over the course of three minutes. The solution heated and nitrogen evolved vigorously. The purple solution was stirred for an additional 45 minutes, followed by the addition of acetic acid (1 ml) to quench any residual diphenyldiazomethane. The solution was extracted with saturated sodium bicarbonate (50 ml), washed with saturated sodium chloride (50 ml), dried over magnesium sulfate and evaporated at reduced pressure to give the crude product (11.24 g). Purification by chromatography on silica gel (95:5; hexane:ethyl acetate) afforded the title compound (6.38 g).

후처리

  1. temperatureThe solution heated
  2. customto quench any residual diphenyldiazomethane
  3. extractionThe solution was extracted with saturated sodium bicarbonate (50 ml)
  4. washwashed with saturated sodium chloride (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated at reduced pressure
  7. customto give the crude product (11.24 g)
  8. customPurification by chromatography on silica gel (95:5; hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-2227aa94be1a4698b61d845789be9ba1
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548751

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