Hydrochloric Acid → HCID 69825368, compound

HRID 2185149Notes

Reaction equation

HRID 2185149 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]1([CH:10]=[CH:11][CH:12]([CH3:16])[CH2:13][CH2:14][OH:15])[CH2:9][CH2:8][CH2:7][CH2:6]1.N1C=CC=CC=1.Cl>CN(C1C=CN=CC=1)C.C1CCCCC1.CC(OC)(C)C>[C:1]([O:15][CH2:14][CH2:13][CH:12]([CH3:16])[CH:11]=[CH:10][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 69825517HCID 69825517, compound

Product 1

HCID 69825368HCID 69825368, compoundYield 96.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8078CyclohexaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Acetyl chloride (1.7 g; 22 mmol) was added to a cooled solution of 5-cyclopentyl-3-methylpent-4-en-1-ol (obtained in example 1; 2.6 g; 15 mmol), pyridine (2.4 g; 30 mmol), and DMAP (0.13 g; 0.1 mmol) in cyclohexane (65 ml). After 3 hours stirring at room temperature, the reaction mixture was poured into 1N HCl (130 ml) and MTBE (65 ml). The organic layer was separated, washed successively with 1N HCl (130 ml), sodium bicarbonate solution (100 ml) and brine (2×100 ml) and treated as in example 1 (distillation at 120° C./0.8 torr) to give 3.05 g (94% yield) of 5-cyclopentyl-3-methylpent-4-en-1-yl acetate.

Workup

  1. customThe organic layer was separated
  2. washwashed successively with 1N HCl (130 ml), sodium bicarbonate solution (100 ml) and brine (2×100 ml)
  3. additiontreated as in example 1 (distillation at 120° C./0.8 torr)

Sources & evidence

ORD record
ord-4b5e4bd03d6f4ac0917f76c494aa1ef0
Source dataset
uspto-grants-2002_06
Patent number
US06399811B1

Reaction notes

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