Formaldehyde → Methyl thenoate

HRID 1190041Notes

Reaction equation

HRID 1190041 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Br)=[CH:8][C:9]=1N(C(CO)CO)C([C@H]1CC[C@H](C)CC1)=O)=[O:4].C=O.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 178499254HCID 178499254, compound

Product 1

HCID 79340Methyl thenoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-3-[(2-hydroxy-1-hydroxymethyl-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (18 mg, 0.041 mmol), paraformaldehyde (6 mg) and boron trifluoride-diethyl etherate (15 μl, 0.12 mmol) in dry dioxane (0.6 mL) was stirred at 80° C. for 14 min. It was cooled and added to ice and NaHCO3 solution mixture, extracted with ethyl acetate, washed with brine, dried and evaporated. Pure 5-bromo-3-[1,3]dioxan-5-yl-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester was obtained after chromatography over silica gel (hexane:ethyl acetate-9:1 as eluent) (15 mg; 81%).

Workup

  1. temperatureIt was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-b0a5d5d74600444fbbebfc23c38c4047
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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