Diethyl Oxalate → HCID 67126246, compound

HRID 514058Notes

Reaction equation

HRID 514058 reaction equation
Br[C:2]1[C:3]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]=[C:7]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:6]=[CH:5]2.[Li]CCCC.[C:36]([O:43][CH2:44][CH3:45])(=[O:42])[C:37]([O:39]CC)=O>C1COCC1>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([C:3]2[C:4]3[C:9](=[CH:8][C:7]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:16])[CH3:17])=[CH:6][CH:5]=3)[CH:10]=[C:11]([CH3:12])[C:2]=2[C:37](=[O:39])[C:36]([O:43][CH2:44][CH3:45])=[O:42])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 56599324HCID 56599324, compoundHCID 178418339Butyllithium

Product 1

HCID 67126246HCID 67126246, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-bromo-5-(4-chlorophenyl)-7-methylnaphthalen-2-yloxy)triisopropylsilane (2.5 g, 4.9 mmol) in THF (50 mL) cooled to −78° C. was added n-BuLi (1.6 M in hexanes, 4.6 mL, 7.4 mmol) dropwise. The resulting solution was allowed to stir at −78° C. for 30 min before addition of diethyl oxalate (1.7 mL, 12.4 mmol). After 45 min at −78° C., the cold bath was removed and the reaction allowed to warm to room temperature over 1 h. 5% citric acid (50 mL) solution was added and the layers separated. Following extraction with EtOAc, the combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The resulting residue was purified by Yamazen column chromatography (0-10% EtOAc/Hex) to afford 2.10 g (81%) of the title compound as a colorless syrup. LCMS-ESI+ (m/z): [M+H]+ calcd for C30H38ClO4Si: 526.16; found: 526.89.

Workup

  1. customthe cold bath was removed
  2. addition5% citric acid (50 mL) solution was added
  3. customthe layers separated
  4. extractionextraction with EtOAc
  5. washthe combined organics were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by Yamazen column chromatography (0-10% EtOAc/Hex)

Sources & evidence

ORD record
ord-1251835de73341019957bb2cb4dbc2d0
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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