Water → HCID 58238629, compound

HRID 41327Notes

Reaction equation

HRID 41327 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1/[N:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Li][C:18]([CH3:21])([CH3:20])[CH3:19].O>C1COCC1.CCCCC>[CH3:19][C:18]([CH3:21])([CH3:20])[CH:6]([NH:5][C:4]1[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=1[O:2][CH3:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 178418306HCID 178418306, compoundHCID 178489586HCID 178489586, compound

Product 1

HCID 58238629HCID 58238629, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

To a solution of 1.27 g (6.00 mmol) of 9 in 40 mL of THF, 4.20 mL (6.30 mmol) of 1.5 M tBuLi in pentane was added with vigorous stirring at −80° C. The mixture was slowly warmed to room temperature, and then 2 mL of water was added. The resulting mixture was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.) to yield 1.50 g (93%) of B1.

Workup

  1. temperatureThe mixture was slowly warmed to room temperature
  2. customThe resulting mixture was evaporated to dryness
  3. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.)

Sources & evidence

ORD record
ord-ab640f051e334e1a82ee542ac64a9fd8
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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