Tetrahydrofuran → HCID 18757876, compound

HRID 433100Notes

Reaction equation

HRID 433100 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:10]2=[C:13]3[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]3[CH2:8][C:9]2=[O:14].[H-].[Na+].[CH2:17](I)[CH2:18][CH3:19].[CH2:21]1[CH2:25]OC[CH2:22]1>>[CH2:17]([C:8]1([CH2:22][CH2:21][CH3:25])[C:7]2[C:13]3[C:3]([CH:4]=[CH:5][CH:6]=2)=[C:2]([Br:1])[CH:12]=[CH:11][C:10]=3[C:9]1=[O:14])[CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 521467HCID 521467, compound

Product 1

HCID 18757876HCID 18757876, compoundYield 80%

Procedure

To a heat dried 8 ml vial loaded with 6-bromo-1,2-dihydroacenaphthylen-1-one (100 mg, 0.41 mmol) and sodium hydride (49 mg, 0.4 mmol) was added 1 ml THF. Propyl iodide (230 μl, 0.4 mmol) was then added to the above purple solution and the mixture was stirred for 1 hour. The reaction was then quenched with 300 ml acetic acid followed by the addition of DCM. The precipitate formed was filtered off and the filtrate concentrated to dryness to give 2.5 grams (80%) of product. NMR and MS confirmed the product.

Workup

  1. customThe reaction was then quenched with 300 ml acetic acid
  2. additionfollowed by the addition of DCM
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-4d625caaa8e94991be279e64fa49760f
Source dataset
uspto-grants-2003_12
Patent number
US06667303B1

Reaction notes

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