Chlorotrimethylsilane → 4-Hydroxy-6-[4-[2-(4-morpholinyl)ethoxy]phenyl]-3-[(phenylmethyl)thio]-2H-pyran-2-one

HRID 613050Notes

Reaction equation

HRID 613050 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[C:34]1([CH2:40][S:41][CH:42]([C:46](O)=[O:47])[C:43](O)=[O:44])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[OH:47][C:46]1[CH:17]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)=[CH:11][CH:12]=2)[O:18][C:43](=[O:44])[C:42]=1[S:41][CH2:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 302564'-(2-Morpholinoethoxy)acetophenoneHCID 2733832Lithium HexamethyldisilazideHCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 546814554-Hydroxy-6-[4-[2-(4-morpholinyl)ethoxy]phenyl]-3-[(phenylmethyl)thio]-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by Method A using 4'-[2-(4-morpholinyl)ethoxy]acetophenone (1.31 g, 5.29 mmol), lithium bis(trimethylsilyl)amide (0.972 g, 5.81 mmol), chlorotrimethylsilane (0.738 mL, 5.81 mmol), THF (58 mL), and diethyl ester of [(phenylmethyl)thio]propanedioic acid (1.35 g, 4.80 mmol). m.p. dec. 207° C.; 1H NMR (250 MHz, DMSO-d6) δ2.54 (s, 2 H), 6.89 (m, 4 H), 2.83 (t, 2 H), 3.55 (m, 4 H), 3.96 (s, 2 H), 4.22 (t, 2 H), 6.58 (s, 1 H), 7.08 (d, 2 H), 7.23 (m, 5 H), 7.73 (d, 2 H).

Workup

  1. custom207° C.

Sources & evidence

ORD record
ord-e510b968f0e04e99a4fda991f0b74894
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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