Methyl chloroformate → HCID 13575671, compound

HRID 465023Notes

Reaction equation

HRID 465023 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([CH3:13])=[CH:8][CH:9]=[C:10]([NH:11][NH2:12])[C:4]=2[O:3]1.C(N(CC)C(C)C)(C)C.Cl[C:24]([O:26][CH3:27])=[O:25]>C1COCC1>[CH3:27][O:26][C:24]([NH:12][NH:11][C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[C:7]([CH3:13])=[CH:8][CH:9]=1)=[O:25]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 13575670HCID 13575670, compound

Product 1

HCID 13575671HCID 13575671, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

15.6 g of 1E was mixed with 150 ml of THF and 11.3 g of N,N-diisopropylethylamine. The mixture was cooled to -5° C. and 9.1 g of methyl chloroformate was added drop-by-drop to the stirred mixture, stirred at 0° C. for two hours, then poured over ice water and extracted with ether. The extract was dried (MgSO4) and the solvent was evaporated. The residue was column chromatographed on silica gel, using a 1:4:20 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane as eluent, to give 2-(2,3-dihydro-2,4-dimethylbenzofuran-7-yl)hydrazinecarboxylic acid methyl ester (1F), as a tan solid, m.p.: 90°-92° C.

Workup

  1. extractionextracted with ether
  2. dry with materialThe extract was dried (MgSO4)
  3. customthe solvent was evaporated
  4. customchromatographed on silica gel
  5. additionv:v mixture of tetrahydrofuran, ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-0e30df148e214556a028d39347442c01
Source dataset
uspto-grants-1985_10
Patent number
US04550121

Reaction notes

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