Water → HCID 86663720, compound

HRID 579518

Reaction equation

HRID 579518 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 86663720HCID 86663720, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-a1b4cfbc95e5416892e2ae720ab25923
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Linked notes

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