Ammonium Chloride → HCID 68835402, compound

HRID 1454100Notes

Reaction equation

HRID 1454100 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=1)[CH2:12][CH:13]([CH3:15])[CH3:14].[C:28]([O:32][C:33](=[O:36])[CH2:34]Br)([CH3:31])([CH3:30])[CH3:29].[Cl-].[NH4+]>C1COCC1>[CH2:11]([O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]([CH2:34][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:36])[C:24]([O:26][CH3:27])=[O:25])=[CH:21][CH:22]=1)[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 78878307HCID 78878307, compound

Product 1

HCID 68835402HCID 68835402, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1.06 M in THF; 9.43 mL, 10.0 mmol) was added dropwise over 10 min to a stirred solution of methyl [4-(isopentyloxy)phenyl]acetate (2.15 g, 9.10 mmol) in THF (30 mL) at −78° C. under nitrogen. On completion of addition stirring was continued at −78 ° C. for 30 min then t-butylbromoacteate (2.12 g, 1.61 mL, 10.9 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 (30 mL) was added and the resulting suspension extracted with ethyl acetate (3×50 mL). The organic phases were combined, dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (20% diethyl ether: cyclohexane) to give the title compound as a colourless oil (2.69 g, 85%). LC/MS: 3.80 min; z/e 351, calcd (M+1) 351. 1H NMR (400 MHz: CDCl3): 7.20 (2H), 6.85 (2H), 3.95 (3H), 3.65 (3H), 3.05 (1H), 2.55 (1H), 1.85 (1H), 1.70 (2H), 1.40 (9H), 0.95 (6H).

Workup

  1. additionOn completion of addition
  2. extractionthe resulting suspension extracted with ethyl acetate (3×50 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel (20% diethyl ether: cyclohexane)

Sources & evidence

ORD record
ord-bea4ed8332d9491d867ec9fbad5c97c5
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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