Methyl chloroformate → HCID 86754070, compound

HRID 1075634Notes

Reaction equation

HRID 1075634 reaction equation
C([Li])CCC.CCCCCC.Br[C:13](Br)=[CH:14][C:15]1[CH:16]=[C:17]([C:20]2([CH3:37])[CH2:24][O:23][C:22]3[CH:25]=[C:26]4[C:31](=[CH:32][C:21]2=3)[C:30]([CH3:34])([CH3:33])[CH2:29][CH2:28][C:27]4([CH3:36])[CH3:35])[S:18][CH:19]=1.Cl[C:40]([O:42][CH3:43])=[O:41].[Cl-].[NH4+]>C1COCC1>[CH3:37][C:20]1([C:17]2[S:18][CH:19]=[C:15]([C:14]#[C:13][C:40]([O:42][CH3:43])=[O:41])[CH:16]=2)[CH2:24][O:23][C:22]2[CH:25]=[C:26]3[C:31](=[CH:32][C:21]1=2)[C:30]([CH3:34])([CH3:33])[CH2:29][CH2:28][C:27]3([CH3:36])[CH3:35]

Participants

7

Reactant 5

HCID 6586Methyl chloroformateHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 86754071HCID 86754071, compoundHCID 178418339Butyllithium

Product 1

HCID 86754070HCID 86754070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2.5 M solution of butyllithium in hexane (0.82 ml, 2.45 mmol) was added to a solution of 3-[4-(2,2-dibromovinyl)thiophen-2-yl]-3,5,5,8,8-pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan (478 mg, 0.94 mmol) in THF (5 ml) at -78° C. The stirring was continued for 1 h at -78° C. and then methyl chloroformate (80 μl) was added. The mixture was stirred at room temperature for 1 h, treated with a saturated ammonium chloride solution and extracted with ethyl ether. After washing with water, the organic phase was dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum. The desired compound was purified by column chromatography.

Workup

  1. extractionextracted with ethyl ether
  2. washAfter washing with water
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator under vacuum
  5. customThe desired compound was purified by column chromatography

Sources & evidence

ORD record
ord-02f84aa352f149afbb2bcc50b0dbc5ad
Source dataset
uspto-grants-1999_05
Patent number
US05905088

Reaction notes

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