Methyl iodide → HCID 86749276, compound

HRID 2396640Notes

Reaction equation

HRID 2396640 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[OH:11][C:12]1[C:20]([CH2:21]/[CH:22]=[C:23]2/[C@H:24]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:26][CH2:27]/2)=[C:19]([O:34][CH3:35])[C:18]([CH3:36])=[C:17]2[C:13]=1[C:14](=[O:37])[O:15][CH2:16]2.[CH3:38]I.[Cl-].[NH4+]>O1CCCC1.CN1CCCN(C)C1=O.C(OCC)(=O)C>[OH:11][C:12]1[C:20]([CH2:21]/[CH:22]=[C:23]2/[C@H:24]([CH:28]([CH3:38])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:26][CH2:27]/2)=[C:19]([O:34][CH3:35])[C:18]([CH3:36])=[C:17]2[C:13]=1[C:14](=[O:37])[O:15][CH2:16]2

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10714445HCID 10714445, compound

Product 1

HCID 86749276HCID 86749276, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

To a solution of 1M sodium bis (trimethylsilyl)amide in tetrahydrofuran (31.7 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H)-pyrimidinone (2.74 ml) at -78° C. was added ethyl (E) 2-{2-[2-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-(S)-yl}acetate (3.39 g) in tetrahydrofuran (35 ml), over a period of 30 minutes. After an additional 30 minutes methyl iodide (2.25 ml) was added. After an additional two hours saturated aqueous ammonium chloride (10 ml) and ethyl acetate were added. The organic solution was dried and evaporated and the residue chromatographed on silica gel, eluting with 4:1 hexane:ethyl acetate, to afford one diastereomer of ethyl (E) 2-{2-[2-(1,3-dihydro-4-hydroxy 6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-(S)-yl}propionate as a low-melting solid.

Workup

  1. customThe organic solution was dried
  2. customevaporated
  3. customthe residue chromatographed on silica gel
  4. washeluting with 4:1 hexane

Sources & evidence

ORD record
ord-56d1876713b84824be79c34870117071
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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