Hydrochloric Acid → HCID 54681477, compound

HRID 613104Notes

Reaction equation

HRID 613104 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:17]2[O:22][C:21](=[O:23])[C:20]([S:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:19]([OH:32])[CH:18]=2)[CH:5]=[C:6]([CH3:16])[C:7]=1[O:8][Si](C)(C)C(C)(C)C.Cl>C1COCC1>[OH:32][C:19]1[CH:18]=[C:17]([C:4]2[CH:3]=[C:2]([CH3:1])[C:7]([OH:8])=[C:6]([CH3:16])[CH:5]=2)[O:22][C:21](=[O:23])[C:20]=1[S:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54681282HCID 54681282, compound

Product 1

HCID 54681477HCID 54681477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (10 mL) solution of 6-[3,5-dimethyl-4-[[dimethyl(1,1-dimethylethyl)silyl]oxy]phenyl]-4-hydroxy-3-[(phenylmethyl)thio]-2H-pyran-2-one at 0° C. is added 3 N HCl (9.0 mL). The reaction is stirred for 48 hrs. at room temperature. The reaction is quenched by pouring onto ethyl acetate and washed in succession with water, saturated sodium chloride; dried over anhydrous magnesium sulfate. After evaporation of the solvents in vacuo, the crude product was purified by flash column chromatography (SiO2 -230 to 400 mesh) using 50% ethyl acetate/hexanes. m.p. 174-176° C.; 1H NMR (250 MHz, DMSO-d6) δ2.21 (s, 6 H), 2.60 (m, 1 H), 3.96 (s, 2 H), 6.52 (s, 1 H), 7.23 (s, 5 H), 7.38 (s, 2 H), 9.06 (s, 1 H).

Workup

  1. customat room temperature
  2. customThe reaction is quenched
  3. additionby pouring onto ethyl acetate
  4. washwashed in succession with water, saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvents in vacuo
  7. customthe crude product was purified by flash column chromatography (SiO2 -230 to 400 mesh)

Sources & evidence

ORD record
ord-1c72d098e0b546a8bef952e787e10892
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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