Water → HCID 86663720、化合物

HRID 579518

反応式

HRID 579518 の反応式
[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1.O>O1CCCC1>[Cl:43][C:40]1[CH:41]=[CH:42][C:37]([O:36][CH2:35][CH2:34][CH:7]([N:8]=[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:22])=[CH:38][CH:39]=1

参加物

6

反応物 4

HCID 962WaterHCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724254Sodium bis(trimethylsilyl)amide

生成物 1

HCID 86663720HCID 86663720、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

While under a nitrogen atmosphere, a solution of (benzhydrylidene-amino)-acetic acid tert-butyl ester (400 mg, 1.35 mmol) in tetrahydrofuran (7 mL) was cooled to −78° C. and treated with sodium bis(trimethylsilyl)amide (1.49 mL, 1.0 M in tetrahydrofuran, 1.49 mmol) in a dropwise manner. After the addition was complete, stirring was continued for 30 minutes and 1-(2-bromoethoxy)-4-chlorobenzene (398 mg, 1.69 mmol) was slowly added to the reaction mixture. Stirring was continued for 2 more hours, then slowly warmed to room temperature overnight. The resulting solution was poured into water, and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (silica gel, 0-20% ethyl acetate in heptane) gave tert-butyl 4-(4-chlorophenoxy)-2-(diphenylmethyleneamino)butanoate as a colorless oil (450 mg. 74%); MS (+CI): m/z for C27H28ClNO3: expected 449.2. found 450.2 (M+H)+, 394.2 (M+H−isobutene)+.

後処理

  1. additionAfter the addition
  2. stirringStirring
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (silica gel, 0-20% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-a1b4cfbc95e5416892e2ae720ab25923
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

関連ノート

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