2-Furanmethanethiol → HCID 53773593, compound

HRID 1415865Notes

Reaction equation

HRID 1415865 reaction equation
C1(P([C:14]2[CH:19]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrC(Br)(Br)Br.[CH:25]1([CH2:31][CH2:32][C:33]([O:39]CC)([O:36][CH2:37][CH3:38])CBr)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[CH3:42][C:43]([O-:46])(C)C.[K+].[CH2:48]([SH:54])[C:49]1[O:53][CH:52]=[CH:51][CH:50]=1.C1C[O:58][CH2:57]C1.CCO>ClCCl>[O:53]1[CH:52]=[CH:51][CH:50]=[C:49]1[CH2:48][S:54][CH2:19][CH2:14][C:32]([C:33]([O:36][CH2:37][CH3:38])=[O:39])([CH2:31][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[C:57]([O:46][CH2:43][CH3:42])=[O:58]

Participants

8

Reactant 6

HCID 73632-FuranmethanethiolHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21873804Tetrahydrofuran ethanolHCID 23665647Potassium tert-butoxideHCID 54420278HCID 54420278, compound2×

Product 1

HCID 53773593HCID 53773593, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using, in the process of example 14, ethyl 3-cyclohexyl-2-ethoxycarbonyl-propionate and 2-trityloxyethyl bromide, 4-cyclohexyl-2,2-diethoxycarbonyl-butan-1-ol is obtained and then by reaction in dichloromethane with triphenylphosphine and tetrabromomethane, 4-cyclohexyl-2,2-diethoxy-1-butyl-bromide. A solution of 0.1 g of potassium tert-butylate in 6 ml of THF/EtOH 1:2 is added with 0.15 g of furfurylmercaptan and 0.38 g of 4-cyclohexyl-2,2-diethoxy-1-butyl bromide. The mixture is refluxed for 4 hours under nitrogen atmosphere, evaporated and partitioned between AcOEt and water. After the usual work up, the solvent is evaporated off and the residue is purified on a silica gel column, to obtain 0.34 g of ethyl 4-(fur-2-ylmethylthio)-2-ethoxycarbonyl-2-cyclohexylmethyl-butanoate.

Workup

  1. temperatureThe mixture is refluxed for 4 hours under nitrogen atmosphere
  2. customevaporated
  3. custompartitioned between AcOEt and water
  4. customAfter the usual work up, the solvent is evaporated off
  5. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-b1901e7aaaad442da2940c4c3e72ddb9
Source dataset
uspto-grants-1999_06
Patent number
US05908863

Reaction notes

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