Ammonium Chloride → HCID 68836040, compound

HRID 1454091Notes

Reaction equation

HRID 1454091 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][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[CH:14][CH:13]=1.[C:29]([O:33][C:34](=[O:37])[CH2:35]Br)([CH3:32])([CH3:31])[CH3:30].[Cl-].[NH4+]>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([CH2:35][C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:37])[C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 14888723HCID 14888723, compound

Product 1

HCID 68836040HCID 68836040, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1.06 M in THF; 20.6 mL, 21.9 mmol) was added dropwise over 10 min to a stirred solution of benzyl (4-bromophenyl)acetate (6.07 g, 19.9 mmol) in THF (60 mL) at −78° C. under nitrogen. On completion of addition stirring was continued at −78° C. for 30 min then t-butylbromoacteate (4.65 g, 3.52 mL, 23.9 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 (6.82 g, 82%). LC/MS: 3.90 min; z/e 419 and 421, calcd (M+1) 419 and 421. 1H NMR (400 MHz: CDCl3): 7.40 (2H), 7.30 (5H), 7.15 (2H), 5.10 (2H), 4.05 (1H), 3.05 (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-ef1dffab73bf48c28c671db6d8d1f5ff
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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