Ammonium Chloride → HCID 68838048, compound

HRID 1454097Notes

Reaction equation

HRID 1454097 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][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=1)[CH2:12][CH:13]([CH3:15])[CH3:14].[CH2:31]([O:38][C:39](=[O:42])[CH2:40]Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+]>C1COCC1>[CH2:11]([O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]([CH2:40][C:39]([O:38][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:42])[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:21][CH:22]=1)[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 62576Benzyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 86032840HCID 86032840, compound

Product 1

HCID 68838048HCID 68838048, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1.06 M in THF; 7.11 mL, 7.54 mmol) was added dropwise over 10 min to a stirred solution of tert-butyl [4-(isopentyloxy)phenyl]acetate (2.00 g, 7.18 mmol) in THF (25 mL) at −78° C. under nitrogen. On completion of addition stirring was continued at −78° C. for 30 min then benzyl-2-bromoacteate (1.97 g, 1.36 mL, 8.61 mmol) was added dropwise over 5 min. The reaction was allowed to warm slowly to room temperature over 4 h. Once at room temperature saturated ammonium chloride solution (25 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 (5-10% diethyl ether: cyclohexane) to give the title compound as a colourless oil (2.00 g, 66%). LC/MS: 4.20 min; z/e 427, calcd (M+1) 427. 1H NMR (400 MHz: CDCl3): 7.35 (5H), 7.2 (2H), 6.80 (2H), 5.10 (2H), 3.95 (3H), 3.15 (1H), 2.65 (1H), 1.85 (1H), 1.65 (2H), 1.45 (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 (5-10% diethyl ether: cyclohexane)

Sources & evidence

ORD record
ord-e7fb84090f874958a5347a988e185c3c
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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