Lithium Hydroxide → 943743-18-8

HRID 735714Notes

Reaction equation

HRID 735714 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:8][C:9]([O:11]CC2C=CC=CC=2)=[O:10])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:8][C:9]([OH:11])=[O:10])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57842903HCID 57842903, compound

Product 1

HCID 57842776943743-18-8Yield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 81A (325 mg, 0.75 mmol) in THF (5 mL) was added LiOH (0.5 mL, 3 mmol). The mixture was stirred rt over night, then concentrated. Water (20 mL) was added to the residue, and the organic phase washed with CH2Cl2 (2×20 mL). The aqueous layer was acidified with 1N HCl, and was extracted with EtOAc (2×20 mL). The combined organic layer washed with brine, dried (Na2SO4) and concentrated to give 81B (262 mg, 100%). 1H NMR (400 MHz, CD3OD) δ ppm 1.36-1.51 (m, 9 H) 3.76-3.99 (m, 2 H) 4.44 (d, J=5.71 Hz, 2 H) 7.18 (d, J=8.35 Hz, 2 H) 7.41-7.49 (m, 2 H).

Workup

  1. concentrationconcentrated
  2. additionWater (20 mL) was added to the residue
  3. washthe organic phase washed with CH2Cl2 (2×20 mL)
  4. extractionwas extracted with EtOAc (2×20 mL)
  5. washThe combined organic layer washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7901340c7924465faf84e89ebf338bcb
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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