Cyclopropanecarbonyl chloride → HCID 14819887, compound

HRID 477500

Reaction equation

HRID 477500 reaction equation
C([Li])CCC.[CH3:6][C:7]1[O:11][N:10]=[CH:9][CH:8]=1.[Li].[Li+].CC([N-]C(C)C)C.[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1>CCCCCC.C1COCC1>[C:7]([CH:8]([C:24]([CH:21]1[CH2:23][CH2:22]1)=[O:25])[C:9]#[N:10])(=[O:11])[CH3:6]

Participants

8

Reactant 5

HCID 77637Cyclopropanecarbonyl chlorideHCID 798335-MethylisoxazoleHCID 2724682Lithium diisopropylamideHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 14819887HCID 14819887, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Buyllithium (19.44 ml, 52.5 mmole of a 2.7 M solution in hexane) was added at -15° C. to a solution of diisopropylalmine (5.31g, 52.5 mmole) in 80 ml of dry THF. After 10 min the cooling bath was lowered to -70° C. and 5-methylisoxazole (4.15 g, 50 mmoles) was added to the lithium diidopropylalmine (LDA) solution followed in 30 min by the dropwise addition of cyclopropanecarboxylic acid chloride (5.33 g, 50 mmoles) in 15 ml of THF. The reaction mixture was then stirred at -78° C. for 30 min and at ambient temperature for 2 h. The solvents were evaporated and the residue was partitioned between ether, 30 ml of water and 13 ml of 4 N NaOH. The aqueous layer was separated, acidified with 6 N HCl and extracted with two portions of ether. The extracts were dried and evaporated to a slushy solid that was cchromatographed on 100 g of silica gel using methylene chloride-Skellysolve B (95:5). The appropriate fractions were combined and concentrated to yield 2.26 g of the title compound as a yellow-tinted solid, mp 62°-63.5° C.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was partitioned between ether, 30 ml of water and 13 ml of 4 N NaOH
  3. customThe aqueous layer was separated
  4. extractionextracted with two portions of ether
  5. customThe extracts were dried
  6. customevaporated to a slushy solid
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-09ac9aefe91141aa93355a3918e89440
Source dataset
uspto-grants-1989_12
Patent number
US04888357

Linked notes

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