Isopropanol hydrochloride → trans-(+/-)-Tetrahydro-5-(phenoxymethyl)-3-furanthiol

HRID 54768Notes

Reaction equation

HRID 54768 reaction equation
[O:1]([CH2:8][C@@H:9]1[O:13][CH2:12][C@@H:11]([S:14]C(=O)C)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].CO.Cl.C(O)(C)C>O1CCCC1>[O:1]([CH2:8][C@@H:9]1[O:13][CH2:12][C@@H:11]([SH:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21912024Isopropanol hydrochlorideHCID 23694274Sodium methanolate methanolHCID 86750316Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-(phenoxymethyl)-3-furanyl]-ester

Product 1

HCID 86750315trans-(+/-)-Tetrahydro-5-(phenoxymethyl)-3-furanthiolYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 16 using 0.532 g of product from Example 23, 506 microliter of 25% sodium methoxide/methyl alcohol, 7.5 ml of tetrahydrofuran, and 1.18 ml of 1.86N hydrochloric acid/isopropyl alcohol to give 0.311 g of the desired product.

Sources & evidence

ORD record
ord-8c4c5437d8414dc68d5a8feb9e0665dd
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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