HCID 14484914, compound → HCID 14484916, compound

HRID 1089614Notes

Reaction equation

HRID 1089614 reaction equation
[C:1]1([S:7][C:8]2[C:16]([OH:17])=[CH:15][C:11]3[CH2:12][CH2:13][O:14][C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1(CSC2C(O)=CC3CCOC=3C=2)C=CC=C[CH:19]=1>>[C:5]1([CH2:6][CH2:1][S:7][C:8]2[C:16]([OH:17])=[CH:15][C:11]3[CH2:12][CH2:13][O:14][C:10]=3[CH:9]=2)[CH:4]=[CH:3][CH:2]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 14484914HCID 14484914, compoundHCID 14484915HCID 14484915, compound

Product 1

HCID 14484916HCID 14484916, compound

Procedure

To a solution of 17 (3.00 g, 11.6 mmol) in dry tetrahydrofuran (50 mL) at -60° was added dropwise a solution of n-butyllithium (1.56 M in hexane, 8.25 mL, 13.0 mmol) and the mixture allowed to stir for 20 minutes. To the resulting white suspension was added dropwise a solution of diphenyl disulfide (4.00 g, 18.5 mmol) in tetrahydrofuran (20 mL) and the mixture allowed to stir for 20 minutes at -60° C. then warmed to room temperature over 40 minutes. The reaction mixture was poured into water (150 mL) and extracted with ether (3×100 mL). The combined extracts were dried (Na2SO4) and concentrated. The crude product (5.0 g) was purified by preparative HPLC using 10% ethyl acetate in hexane as eluant then directly deprotected in methanol (40 mL) containing concentrated HCl (0.25 mL) at 50° C. for 3 hours. Most of the methanol was removed in vacuo and the residue partitioned between ethyl acetate (75 mL) and water (25 mL). The organic extract was washed with an additional portion of water (25 mL), dried (Na2SO4), and concentrated. Flash chromatography using 10% ethyl acetate in hexane afforded 18a. 18a: mp 80°-81° C. Recrystallization from hexane gave an analytical sample. 2,3-Dihydro-6-phenylmethylthio-5-benzofuranol (18b); 2,3-dihydro 6 (2 phenylethyl)thio-5-benzofuranol (18c) and 2.3-dihydro-6-3-phenylpropyl)thio-5 -benzofuranol (18d) can be produced from 17 in similar fashion. 18b: mp 50°-52° C.; 18c and 18d are oils.

Workup

  1. customRecrystallization from hexane
  2. customgave an analytical sample

Sources & evidence

ORD record
ord-384d504d31bc4dbeb2daad5d5e5ca8b8
Source dataset
uspto-grants-1990_10
Patent number
US04966907

Reaction notes

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