Methyl iodide → HCID 86749276, compound

HRID 1781552Notes

Reaction equation

HRID 1781552 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-089ee3ae5afb430eb9502365490c6f0d
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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