Boron trifluoride etherate → Ethanethioic acid S-[tetrahydro-5-(hydroxymethyl)-3-thienyl]ester

HRID 1290399Notes

Reaction equation

HRID 1290399 reaction equation
C1(C[O:8][CH2:9][CH:10]2[S:14][CH2:13][CH:12]([S:15][C:16](=[O:18])[CH3:17])[CH2:11]2)C=CC=CC=1.B(F)(F)F.CCOCC>C(Cl)(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:8][CH2:9][CH:10]1[S:14][CH2:13][CH:12]([S:15][C:16](=[O:18])[CH3:17])[CH2:11]1

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 54092544Ethanethioic acid S-[tetrahydro-5-[(phenylmethoxy)methyl]-3-thienyl]ester

Product 1

HCID 54469016Ethanethioic acid S-[tetrahydro-5-(hydroxymethyl)-3-thienyl]ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6212ChloroformSolvent

Procedure

A 0° C. solution, under argon, of 0.123 g of product from Example 139 in 1.0 ml of dry chloroform is treated with 51.1 microliter of boron trifluoride etherate and 0.193 g of tetra n-butylammonium iodide. the reaction mixture is stirred at room temperature overnight and concentrated in vacuo. The residue is purified by chromatography (silica gel: 0-100% ethyl acetate/hexane) to give 0.079 g of the desired. product.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by chromatography (silica gel: 0-100% ethyl acetate/hexane)
  3. customto give 0.079 g of the

Sources & evidence

ORD record
ord-b3d761b8773240b7918086a42f92c1c1
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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