Acetonitrile → HCID 86646688, compound

HRID 1677506Notes

Reaction equation

HRID 1677506 reaction equation
CC1(C=O)CC[C:4]2([O:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][O:7]2)C1.[C:16]([O-:19])([O-])=O.[K+].[K+].BrCCCCBr.C[C:29]#[N:30]>O>[CH3:4][O:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]([N:30]([O:19][CH3:16])[CH3:29])=[O:7]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 80561,4-Dibromobutane2×HCID 11430Potassium CarbonateHCID 595406622,8,8-Trimethyl-6,10-dioxa-spiro[4.5]decane-2-carbaldehyde

Product 1

HCID 86646688HCID 86646688, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Step 3—A mixture of 2 (0.9 g, 3.912 mmol), K2CO3 (0.595 g, 4.303 mmol) and 1,4-dibromobutane (0.49 mL, 4.108 mmol) in 14 mL of CH3CN and 1 mL of H2O was stirred at 110° C. for 30 minutes under microwave irradiation before being cooled to RT. 0.5 more equivalents of 1,4-dibromobutane were added and the resulting mixture was stirred at 110° C. for 30 minutes under microwave irradiation a second time before being cooled to RT. The reaction mixture was extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by SiO2 chromatography (hexanes/EtOAc 0-8% EtOAc) to give 0.25 g of 3: 3-bromo-5-pyrrolidin-1-yl-benzoic acid methyl ester (22% yield).

Workup

  1. temperaturebefore being cooled to RT
  2. stirringthe resulting mixture was stirred at 110° C. for 30 minutes under microwave irradiation a second time
  3. temperaturebefore being cooled to RT
  4. extractionThe reaction mixture was extracted twice with DCM
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by SiO2 chromatography (hexanes/EtOAc 0-8% EtOAc)

Sources & evidence

ORD record
ord-a7fe6812273c45c6aed870a8ad795090
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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