Acetone → HCID 10753833, compound

HRID 1884318Notes

Reaction equation

C[C:2]1([CH3:33])[CH:11]2[O:12][C:13](=[O:14])[C:5]3([CH:10]2[CH:9]2[CH2:15]CC4C5(C)CCC(O)C(C)(C)C5CCC4(C)[C:8]2(C)CC3)CC1.[CH2:34](Br)[CH:35]=[CH2:36].[C:38]([O-])([O-])=O.[K+].[K+].[CH3:44][C:45]([CH3:47])=[O:46]>N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>[CH2:34]([O:46][C:45]1[C:47]([CH3:38])=[C:10]2[C:11](=[C:2]([CH3:33])[CH:44]=1)[O:12][C:13](=[O:14])[CH2:5][C:9]2([CH3:8])[CH3:15])[CH:35]=[CH2:36]

Participants

Conditions

Temperature: 60 °C

Procedure

The lactone A (7.08 g, 32.17 mmol) and allyl bromide (7.79 g, 64.35 mmol) were dissolved in 50 mL of acetone. K2CO3 (8.88 g, 64.35 mmol) and Nal (0.2 g) were added into the solution. The mixture was stirred at 60° C. for 80 h and then evaporated. The residue was partitioned between water and methylene chloride. The organic layer was separated. The aqueous layer was further extracted with methylene chloride (4×50 mL), and the combined CH2Cl2 layers were washed with water (3×50 mL) and dried over MgSO4. Solvent evaporation gave 8.26 g (99%) of a white solid (B). 1H NMR 500 MHz (CDCl3) δ6.63 (s, 1H), 6.13-6.01 (m,1H), 5.46-5.26 (m, 2H), 4.50 (d, J=5.1 Hz, 2H), 2.56 (s, 2H), 2.35 (s, 3H), 2.27 (s, 3H), 1.46 (s, 6H).

Workup

customevaporated
customThe residue was partitioned between water and methylene chloride
customThe organic layer was separated
extractionThe aqueous layer was further extracted with methylene chloride (4×50 mL)
washthe combined CH2Cl2 layers were washed with water (3×50 mL)
dry with materialdried over MgSO4
customSolvent evaporation

Sources & evidence

ORD record: ord-dd7871cb8cce4eb7a7add0b19a55e455
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06764768B2

Reaction notes

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