Diisopropylamine → HCID 9839387, compound

HRID 359157Notes

Reaction equation

HRID 359157 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.COC1C=CC(C[C:22]2([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]2[C:28](OCC)=[S:29])=CC=1.[C:42]([O:45]C(=O)C)(=[O:44])[CH3:43]>O1CCCC1>[C:42]([O:45][C:22]1[C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:28]=2[S:29][C:33]=1[C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1)(=[O:44])[CH3:43]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 7918Acetic AnhydrideHCID 86744663HCID 86744663, compoundHCID 178418339Butyllithium

Product 1

HCID 9839387HCID 9839387, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.5 mL (10.7 mmol) of diisopropylamine in 10 mL of dry tetrahydrofuran was cooled to -78° under nitrogen. To this was added 4 mL of 2.5M n-butyllithium (in hexane) and after 15 minutes, a solution of 1.36 g (3 mmol) of ethyl 2,2-bis-(4-methoxyphenyl)methylthiocyclohexanecarboxylate in 5 mL of dry tetrahydrofuran was added and the solution was stirred under N2 for 2 hours. Then 1.5 mL (15 mmol) of acetic anhydride was added and the solution was stirred at room temperature for 1 hour. The solution was partitioned between ether and NaHCO3 and the ether layer was washed with NaHCO3, then brine, and dried over MgSO4. The solution was concentrated and the residue chromatographed on silica gel (20% ethyl acetate-hexane) to afford a colorless oil. This was crystallized from ethyl acetate-hexane to afford 0.394 g (47%) of title compound as a white crystalline solid, m.p. 81° C. NMR (CDCl3, (CH3)4Si) δ1.81 (4H, m), 2.25 (3H, s, CH3CO), 2.35 (2H, t, J=6Hz), 2.71 (2H, t J=6Hz), 3.80 (3H, s, OCH3), 6.90 (2H, AB), 7.39 (2H, AB).

Workup

  1. stirringthe solution was stirred at room temperature for 1 hour
  2. customThe solution was partitioned between ether and NaHCO3
  3. washthe ether layer was washed with NaHCO3
  4. dry with materialbrine, and dried over MgSO4
  5. concentrationThe solution was concentrated
  6. customthe residue chromatographed on silica gel (20% ethyl acetate-hexane)
  7. customto afford a colorless oil
  8. customThis was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d6c8ab605d8842368f00f62d3f98b2dc
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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