1,2-Dimethoxyethane → HCID 86761861, compound

HRID 2097522Notes

Reaction equation

HRID 2097522 reaction equation
COCCOC.[CH2:7]([O:14][CH2:15][N:16]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[C:18]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:17]1[CH:35]=[O:36])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:37][C:38]1[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=1[CH2:40]Br.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:7]([O:14][CH2:15][N:16]1[CH:20]=[C:19]([CH2:40][C:39]2[CH:42]=[CH:43][CH:44]=[CH:45][C:38]=2[F:37])[C:18]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:17]1[CH:35]=[O:36])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 86761862HCID 86761862, compound

Product 1

HCID 86761861HCID 86761861, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 100 ml of 1,2-dimethoxyethane solution containing 4.38 g (10.6 mmol) of ethyl 1-benzyloxymethyl-2-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrol-3-carboxylate obtained in Reference example 36-(c) were added 2.60 ml (21.4 mmol) of 2-fluorobenzyl bromide and 100 ml of 2M sodium carbonate aqueous solution, the mixture was degassed under reduced pressure and replaced with argon. Further, 2.47 g (2.14 mmol) of tetrakistriphenylphosphine palladium was added to the mixture, and the resulting mixture was stirred at 50° C. for 3 hours. After completion of the reaction, to the reaction mixture were added water and a saturated aqueous solution of sodium chloride, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1→4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 3.80 g of the title compound as a yellowish oil. (Yield: 91%)

Workup

  1. customthe mixture was degassed under reduced pressure
  2. customAfter completion of the reaction
  3. extractiona saturated aqueous solution of sodium chloride, and the mixture was extracted with ethyl acetate
  4. customThe organic layer after separation
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c341bb319c94d5d8339ed85fb01471e
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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