Sulfuric Acid → 1-(Thiophen-3-yl)cyclopropan-1-ol

HRID 1986665Notes

Reaction equation

HRID 1986665 reaction equation
C(O[C:4]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=[O:5])C.[CH2:11]([Mg]Br)[CH3:12].S(=O)(=O)(O)O>C(OCC)C>[S:8]1[CH:9]=[CH:10][C:6]([C:4]2([OH:5])[CH2:12][CH2:11]2)=[CH:7]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 798243-Thiophenecarboxylic acid, ethyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 574375501-(Thiophen-3-yl)cyclopropan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1.37 ml (10.00 mmol) ethylthiophene-3-carboxylate and 0.29 ml (1.00 mmol)titanium tetra-isopropyloxide are placed in 5 ml diethyl ether, 21.20 ml (21.20 mmol) ethylmagnesium bromide (Grignard reagent in tetrahydrofuran) in 15 ml diethyl ether are added dropwise within 1 hour, while the temperature should not rise above 20° C. The reaction mixture is stirred for 1.5 hours, then hydrolysed with 10% sulphuric acid. The aqueous phase is extracted with diethyl ether, the combined organic phases are dried and evaporated to dryness. The residue is purified by chromatography. Yield: 0.330 g (24% of theoretical)

Workup

  1. customrise above 20° C
  2. extractionThe aqueous phase is extracted with diethyl ether
  3. customthe combined organic phases are dried
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-2a06da8ace2f4871b83320ede1819e42
Source dataset
uspto-grants-2009_06
Patent number
US07550472B2

Reaction notes

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