Tetrahydrofuran → HCID 22978424, compound

HRID 1860681Notes

Reaction equation

HRID 1860681 reaction equation
[CH:1]([Mg]Br)=[CH2:2].O1CC[CH2:7][CH2:6]1.O1CCCC1.C(O[C:18](=[O:33])[C:19]([C:31]#[N:32])=[C:20]([CH3:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)C.Cl.[OH2:35]>[I].[Cu].C(OCC)C>[CH2:6]([O:35][C:18](=[O:33])[CH:19]([C:31]#[N:32])[C:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)([CH3:30])[CH:1]=[CH2:2])[CH3:7]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 21885828Hydrate;hydrochlorideHCID 600747842-Cyano-4-(4-methoxy-phenyl)-3-methyl-but-2-enoic Acid Ethyl EsterHCID 178420667HCID 178420667, compound

Product 1

HCID 22978424HCID 22978424, compound

Reagents, catalysts & solvents 2

HCID 178505378HCID 178505378, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1 M vinyl magnesium bromide/tetrahydrofuran (38.6 ml), copper iodine (0.08 g), and tetrahydrofuran (50 ml) was added the solution of product produced in STEP 1 (10.0 g) and ethyl ether (20 ml). The resulting solution was stirred at room temperature overnight. The solution was poured into 5% hydrochloric acid/water (100 ml). The organic layer was separated and the aqueous portion was extracted well with ethyl ether and the combined organic extract was washed with water, brine and dried over MgSO4. The crude product was purified on a silica gel column, eluting with 10% ethyl acetate/hexane to afford light yellow oil (6.3 g). The 1H NMR was consistent with the proposed structure.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous portion was extracted well with ethyl ether
  3. extractionthe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over MgSO4
  6. customThe crude product was purified on a silica gel column
  7. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-15853ae3ea9a453d8481626b2461b191
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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