Ammonium Chloride → HCID 68636260, compound
Reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[Li].C([Mg]Cl)C=C.[CH3:14][C:15]1[CH:16]([C:25](OCC)=[O:26])[C:17]2([CH2:22][CH2:23][CH:24]=1)[CH2:21][CH2:20][CH2:19][CH2:18]2.[NH4+].[Cl-]>C1COCC1.CC(OC)(C)C>[CH3:14][C:15]1[CH2:24][CH2:23][CH2:22][C:17]2([CH2:21][CH2:20][CH2:19][CH2:18]2)[C:16]=1[C:25](=[O:26])/[CH:7]=[CH:5]/[CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 33 °C
Procedure
At 20° C., a solution of lithium diisopropylamine (9.3 ml, 2M in THF/heptane) was treated dropwise within 10 min. with a solution of allylmagnesium chloride (15 ml, 2 M in THF). The resulting mixture was heated at 33° C., treated dropwise with a solution of ethyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (6 g, 27 mmol) in THF (7 ml), stirred at 20° C. for 1 h and at 40° C. for 24 h, treated with a mixture of allylmagnesium chloride (15 ml, 2 M in THF) and lithium diisopropylamine (9.3 ml, 2M in THF/heptane), stirred at 30° C. for 2 h, poured into a mixture of a saturated aqueous solution of NH4Cl (100 ml) and ice (115 g), and diluted with MTBE (200 ml). The organic phase was washed with 10% aqueous HCl (80 ml), with a saturated aqueous solution of NaHCO3 (80 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4) and concentrated. FC (SiO2, hexane/MTBE 100:1 to 90:10) of the crude product (8.3 g) gave (E)-1-(7-methylspiro[4.5]dec-7-en-6-yl)but-2-en-1-one and (E)-1-(7-methylspiro[4.5]dec-6-en-6-yl)but-2-en-1-one (1 g, 17%).
Workup
- stirringstirred at 30° C. for 2 h
- washThe organic phase was washed with 10% aqueous HCl (80 ml), with a saturated aqueous solution of NaHCO3 (80 ml), with a saturated aqueous solution of NaCl (50 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-09d61358463a437788b9d8ecc40a2ebb
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012391B2
Reaction notes
Loading…