Ammonium Chloride → HCID 68834130, compound

HRID 1454086Notes

Reaction equation

HRID 1454086 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=1.[CH2:26]([O:33][C:34](=[O:37])[CH2:35]Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([CH2:35][C:34]([O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:37])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 62576Benzyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 14775457tert-butyl 2-(4-bromophenyl)acetate

Product 1

HCID 68834130HCID 68834130, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1.06 M in THF; 18.1 mL, 19.2 mmol) was added dropwise over 10 min to a stirred solution of tert-butyl (4-bromophenyl)acetate (4.92 g, 18.1 mmol) in THF (50 mL) at −78 ° C. under nitrogen. On completion of addition stirring was continued at −78 ° C. for 30 min then benzyl-2-bromoacteate (4.97 g, 3.44 mL, 21.7 mmol) was added dropwise over 5 min. The reaction was allowed to warm slowly to room temperature over 4 h then saturated ammonium chloride solution (50 mL) was added and the resulting suspension extracted with ethyl acetate (3×100 mL). The organic phases were combined, dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (10% diethyl ether: cyclohexane) to give the title compound as a colourless oil (6.26 g, 82%). LC/MS: 4.02 min; z/e 419 and 421, calcd (M+1) 419 and 421. 1H NMR (400 MHz: CDCl3): 7.40 (2H), 7.30 (5H), 7.10 (2H), 5.10 (2H), 3.90 (1H), 3.15 (1H), 2.65 (1H), 1.35 (9H).

Workup

  1. additionOn completion of addition
  2. extractionthe resulting suspension extracted with ethyl acetate (3×100 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel (10% diethyl ether: cyclohexane)

Sources & evidence

ORD record
ord-8193e104de6948e695499afe63b80b41
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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