Sodium Bicarbonate → 6-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-hydroxyphenyl Ketone

HRID 1387106Notes

Reaction equation

HRID 1387106 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]([C:22]2[C:23]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:41][C:24]=3[S:25][C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:29][CH:28]=2)=[O:21])[CH:6]=[CH:7][C:8]=1[O:9][Si](C(C)C)(C(C)C)C(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]([C:22]2[C:23]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:41][C:24]=3[S:25][C:26]=2[C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:31][CH:32]=2)=[O:21])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 183184746-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-methoxy-4-triisopropylsilyloxyphenyl ketone

Product 1

HCID 183184716-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-hydroxyphenyl Ketone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-methoxy-4-triisopropylsilyloxyphenyl ketone (Part C; 4.89 g; 6.64 mmol) in 65 mL of dry THF was treated with tetrabutylammonium fluoride (1 M solution in THF; 7.3 mL) in a dropwise fashion. After 10 min, the reaction mixture was poured into 100 mL of saturated NaHCO3 (aq). The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were dried over K2CO3, filtered and concentrated in vacuo to give a quantitative yield of the title compound as a orange foam. An analytical sample was purified by radial chromatography (SiO2; gradient of 1% to 3% MeOH in CHCl3).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  2. dry with materialThe combined organic layers were dried over K2CO3
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7474df19131443d3ba49f518e559ce3e
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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