Water → HCID 21706312, compound

HRID 1595053Notes

Reaction equation

HRID 1595053 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:15]4[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:32]([Si]([O:42][Si](C(C)C)(C(C)C)C(C)C)(C(C)C)C(C)C)([CH3:34])[CH3:33].[C:53]([O-:56])([O-:55])=[O:54].[Cs+].[Cs+].O>CN(C=O)C>[C:22]([OH:25])(=[O:42])[C:53]([OH:56])=[O:55].[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:15]4[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:33][CH2:32][CH2:34][OH:54])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 14400419HCID 14400419, compoundHCID 224626554-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenol

Product 1

HCID 21706312HCID 21706312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenol (0.25 g; 0.58 mmol), 0.21 g (0.70 mmol) of the triisopropylsilyl ether prepared above and Cs2CO3 (1.33 g; 4.07 mmol) were combined in 5 mL of DMF in a flame-dried, argon-filled flask and heated in an oil bath maintained at 70° C. for 2 h. After cooling to room temperature, water was added (25 mL) and extraction was carried out with EtOAc (4×25 mL). The combined organics were dried by passage through Na2SO4. The triisopropylsilyl protecting group was removed by stirring with an excess of tetrabutylammonium fluoride in THF at room temperature for 0.5 h. The product was isolated as a colorless oil (165 mg; 58%) by flash chromatography on silica gel, eluting with EtOAc(10-90%)/Et3N(0-5%)/MeOH(0-5%). Conversion to the oxalate was effected in the usual way.

Workup

  1. additionfilled flask
  2. temperatureheated in an oil bath
  3. temperatureAfter cooling to room temperature
  4. extraction(25 mL) and extraction
  5. dry with materialThe combined organics were dried by passage through Na2SO4
  6. customThe triisopropylsilyl protecting group was removed
  7. customThe product was isolated as a colorless oil (165 mg; 58%) by flash chromatography on silica gel
  8. washeluting with EtOAc(10-90%)/Et3N(0-5%)/MeOH(0-5%)

Sources & evidence

ORD record
ord-e23995a798de4bd1be5dff0488d2c99b
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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