Methyl chloroformate → HCID 22467242, compound

HRID 381306Notes

Reaction equation

HRID 381306 reaction equation
C([Li])(CC)C.Br[C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][CH3:17])=[CH:9][CH:8]=1.Cl[C:19]([O:21][CH3:22])=[O:20]>C1CCCCC1.C(OCC)C>[CH3:22][O:21][C:19]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][CH3:17])=[CH:9][CH:8]=1)=[O:20]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 18007603HCID 18007603, compound2×HCID 178418400CID 53628100

Product 1

HCID 22467242HCID 22467242, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8078CyclohexaneSolvent

Procedure

Sec-butyllithium (9.4 ml of a 1.3M solution in cyclohexane) was added to a stirred solution of 6-bromo-1-ethylindole [the compound of step (a), 2.5 g]in diethylether (20 ml) at −78° C. under a nitrogen atmosphere. After 30 minutes this solution was transferred by cannula to a stirred solution of methyl chloroformate (1.29 ml, 16.74 mmol) in diethyl ether (8 ml) at −78° C. under a nitrogen atmosphere. After 1 hour the cooling bath was removed and the mixture was allowed to warm to room temperature. After a further 1 hour the mixture was poured into brine and extracted with ethyl acetate. The organic layers were dried (MgSO4 ) and concentrated in vacuo to give a yellow oil. Flash column chromatography (elution with 90% hexane, 10% ethyl acetate) gave 1.76 g of the subtitle compound as a pale yellow oil.

Workup

  1. customAfter 1 hour the cooling bath was removed
  2. additionAfter a further 1 hour the mixture was poured into brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layers were dried (MgSO4 )
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. washFlash column chromatography (elution with 90% hexane, 10% ethyl acetate)

Sources & evidence

ORD record
ord-0a6cea641622424c8817b56dd9a8a7a6
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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