Lithium diisopropylamide mono(tetrahydrofuran) → HCID 59128314, compound

HRID 1990922Notes

Reaction equation

HRID 1990922 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[C:18]([Cl:19])[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26](=[O:28])=[O:27].CC(C)=O.[Li+:33].CC([N-]C(C)C)C.C1COCC1>C1COCC1>[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[C:18]([Cl:19])[C:13]=3[CH:12]=[C:11]2[C:26]([O-:28])=[O:27])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+:33]

Participants

5

Reactant 3

HCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 18522661Acetone cardiceHCID 20612406HCID 20612406, compound

Product 1

HCID 59128314HCID 59128314, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the N-sulfonyl compound 24 (1.504 g, 4.07 mmol) in dry THF (150 mL), cooled by dry ice/acetone, is added LDA-THF (3.8 mL, 1.5M solution in cyclohexane, 5.7 mmol). After 45 min, carbon dioxide is bubbled into the solution for 5 min, then the cooling bath is removed. When the solution has reached ambient temp., the solvents are evaporated, yielding 1.73 g of the salt 27 [containing (iPr)2NCO2Li] as pale yellow solid. The salt is used without purification in the next step. 1H-NMR (D6-DMSO): δ=6.44 (s, 1H), 7.50-7.75 (m, 6H), 8.33-8.40 (m, 2H), 8.53 (dd, J=8.0, 1.6 Hz, 2H).

Workup

  1. customcarbon dioxide is bubbled into the solution for 5 min
  2. customthe cooling bath is removed
  3. customhas reached ambient temp.
  4. customthe solvents are evaporated

Sources & evidence

ORD record
ord-6d4a934dc0494b3b931fe894d55fbb3e
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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