Ammonium Chloride → HCID 67065031, compound

HRID 546814Notes

Reaction equation

HRID 546814 reaction equation
[C:1]([Si:5]([CH3:41])([CH3:40])[O:6][CH:7]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=3)=[C:23]([CH3:34])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:35])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl-].[CH3:53][O:54][CH2:55][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([Si:5]([O:6][CH:7]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH2:17][CH3:18])([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[O:31][C:30]([CH:32]=[CH:53][O:54][CH3:55])=[CH:29][CH:28]=3)=[C:23]([CH3:34])[CH:22]=2)[CH2:19][CH3:20])=[CH:12][C:11]=1[CH3:35])[C:36]([CH3:38])([CH3:39])[CH3:37])([CH3:40])[CH3:41])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 57708991HCID 57708991, compound

Product 1

HCID 67065031HCID 67065031, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-[4-(1-{4-[3-(t-Butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-furan-2-carbaldehyde (Example 3-(6); 47.4 mg, 0.082 mmol) was added to a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 0.36 mL, 0.18 mmol) and (methoxymethyl)triphenylphosphonium chloride (56.2 mg, 0.164 mmol) in toluene (0.5 mL) at room temperature, and the mixture was stirred for 30 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane only to hexane/ethyl acetate=9/1) to give the title compound (42 mg, 85%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by a silica gel column (hexane only to hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-24a580d88ab84562b0455872d0310ef5
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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