Diisopropylamine → Lithium diisopropylamide

HRID 1796848Notes

Reaction equation

HRID 1796848 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Li:8]CCCC.[CH3:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(C1CCC([CH:28]2CC[CH:31]([C:34](F)([F:36])[F:35])[CH2:30][CH2:29]2)CC1)CC.C1COCC1.[CH3:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>>[CH:1]([N-:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Li+:8].[CH2:15]([CH:16]1[CH2:43][CH2:44][CH:45]([CH:46]2[CH2:28][CH2:29][CH:30]([CH:31]=[C:34]([F:36])[F:35])[CH2:48][CH2:47]2)[CH2:18][CH2:17]1)[CH2:14][CH3:13]

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8058HexaneHCID 21883165Tetrahydrofuran hexaneHCID 221828671,1′-Bicyclohexyl, 4-propyl-4′-(trifluormethyl)-, (trans,trans)-HCID 178418339Butyllithium

Product 2

HCID 2724682Lithium diisopropylamideYield 98%HCID 10880172HCID 10880172, compound

Conditions

Temperature
-10 °C

Procedure

A solution of lithium diisopropylamide in THF/hexane was prepared from diisopropylamine (0.8 mL, 5.475 mmol) and 2.5M BuLi (2.2 mL, 5.475 mmol) at −50° C. The solution was brought to −10° C. and a hexane solution of 4(4′-propylcyclohexyl)-1-trifluoromethylcyclohexane (1.0 g, 3.65 mmol in 2 mL) was added followed by addition of KtBuO (0.614 mg, 5.475 mmol). The mixture was stirred for 10 min. then brought to RT for 30 min. The reaction was monitored by GCMS for completion. After cooling again to −10° C., the reaction was quenched by addition of water (2 mL), extracted into hexane (10 mL); dried (MgSO4), filtered and the solvent was distilled to obtain the product in 98% yield by GC. The crude product in hexane was filtered through a plug of silica gel to obtain the pure compound, i.e., 4(4′-propylcyclohexyl)-1-difluorovinylcyclohexane.

Workup

  1. customwas brought to −10° C.
  2. additionfollowed by addition of KtBuO (0.614 mg, 5.475 mmol)
  3. waitthen brought to RT for 30 min
  4. customthe reaction was quenched by addition of water (2 mL)
  5. extractionextracted into hexane (10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. distillationthe solvent was distilled
  9. customto obtain the product in 98% yield by GC
  10. filtrationThe crude product in hexane was filtered through a plug of silica gel

Sources & evidence

ORD record
ord-baf22fa6daf8405d9b63814063500414
Source dataset
uspto-grants-2006_04
Patent number
US07030283B2

Reaction notes

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