Hydrochloric Acid → HCID 69659336, compound

HRID 1829039Notes

Reaction equation

HRID 1829039 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.O1CCCCC1[O:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[C:41](=O)[O:40][CH2:39]2.Cl>C(COC)OC.C1COCC1>[OH:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[C:41](=[C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]1=[O:10])[O:40][CH2:39]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 321710OxindoleHCID 220614825-{3-[(Oxan-2-yl)oxy]propyl}-2-benzofuran-1(3H)-oneHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 69659336HCID 69659336, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of oxindole (401 mg, 3.0 mmol) in anhydrous dimethoxyethane (20 ml) under nitrogen was added 1.0M LiHMDS/THF solution (6.3 ml, 6.3 mmol). The mixture was stirred at room temperature for 10 minutes, and 5-[3-(tetrahydro-pyran-2-yloxy)-propyl]-3H-isobenzofuran-1-one (500 mg, 1.81 mmol) was added. After stirred at room temperature for 2.5 hours, the mixture was poured into a mixture of THF (30 ml) and 2M HCl aqueous solution (30 ml) and heated at 65° C. for 1 hour. The mixture was cooled to room temperature, and then poured into an ice water (300 ml). The resulting solid was separated, rinsed with water, and dried to give 3-[5-(3-hydroxy-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a yellow solid (460 mg, 83%).

Workup

  1. stirringAfter stirred at room temperature for 2.5 hours
  2. temperatureheated at 65° C. for 1 hour
  3. temperatureThe mixture was cooled to room temperature
  4. customThe resulting solid was separated
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-22cde4261f4340e3963fb2342a4f0c2d
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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