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

HRID 464567ノート

反応式

HRID 464567 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2227aa94be1a4698b61d845789be9ba1
出典データセット
uspto-grants-1985_10
特許番号
US04548751

反応ノート

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