Ethyl Acetate → HCID 57708944, compound

HRID 546816Notes

Reaction equation

HRID 546816 reaction equation
[H-].[Na+].[C:3]([Si:7]([CH3:43])([CH3:42])[O:8][CH:9]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[O:33][C:32]([CH:34]=O)=[CH:31][CH:30]=3)=[C:25]([CH3:36])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:37])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+].[C:46]([O:49][CH2:50][CH3:51])(=[O:48])[CH3:47]>O1CCCC1>[CH2:50]([O:49][C:46](=[O:48])/[CH:47]=[CH:34]/[C:32]1[O:33][C:29]([C:26]2[CH:27]=[CH:28][C:23]([C:18]([C:15]3[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH:9]([O:8][Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:43])[CH3:42])[C:38]([CH3:39])([CH3:41])[CH3:40])=[C:13]([CH3:37])[CH:14]=3)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:24][C:25]=2[CH3:36])=[CH:30][CH:31]=1)[CH3:51]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57708991HCID 57708991, compound

Product 1

HCID 57708944HCID 57708944, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% in oil, 8.4 mg, 0.209 mmol) was added to tetrahydrofuran (1 mL) at 0° C. Triethyl phosphonoacetate (0.049 mL, 0.244 mmol) and then a solution of 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); 100 mg, 0.174 mmol) in tetrahydrofuran (0.6 mL) were added at the same temperature, and the mixture was stirred for 20 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was 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 (112 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-68551b0194834dd2a66ba8fb8425ac64
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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