Butyl ether → HCID 67105312, compound

HRID 41332Notes

Reaction equation

HRID 41332 reaction equation
[O:1]([C:8]1[C:21](C(C)(C)C)=[CH:20][C:19]([CH3:26])=[CH:18][C:9]=1/[N:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(CCCC)CCCC.[C:36]1([Li])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1COCC1>[O:1]([C:8]1[CH:21]=[CH:20][C:19]([CH3:26])=[CH:18][C:9]=1[NH:10][CH:11]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8909Butyl etherHCID 178428447HCID 178428447, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 67105312HCID 67105312, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12 (300 mg, 1.12 mmol) in THF was added 1.24 mL of a 1.8M nBu2O solution of phenyl lithium at −40° C. After stirring for 15 min, the reaction was quenched with water (1 mL). MgSO4 was added and the mixture filtered to give a yellow solution. Removal of the solvent under vacuum gave C1 as a yellow oil (240 mg, 62% yield).

Workup

  1. customthe reaction was quenched with water (1 mL)
  2. additionMgSO4 was added
  3. filtrationthe mixture filtered
  4. customto give a yellow solution
  5. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-c5232832fca548b79ed267a5fde13118
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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