Water → HCID 22902253, compound
Reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:14][CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:12]#N)[CH:7]=[CH:8][C:9]=1[Cl:10].Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O.C[N:34](C)C=O>>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[O:16][CH2:15][CH2:14][C:11]1[C:6]([CH:7]([C:8]#[N:34])[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:5][C:4]([Cl:3])=[C:9]([Cl:10])[CH:12]=1Participants
6
Procedure
4.6 g of 60% NaH are added in small portions to a solution of 36 g of the above 3,4-dichloro-α-[(2-tetrahydropyranyloxy)ethyl]benzeneacetonitrile (prepared according to PREPARATION II (a)) in 100 ml of dimethylformamide. The reaction mixture is stirred for 3 hours at room temperature and cooled to 0° C. and 22.4 g of ethyl 4-bromobutyrate in 40 ml of dimethyl-formamide are then added. The reaction mixture is stirred for 3 hours at room temperature, poured into water and extracted with ether and the extract is washed with a saturated solution of NaCl, dried over Na2SO4 and concentrated under vacuum. The residue obtained is purified by chromatography on silica gel using toluene as the eluent to give 24 g of the expected product.
Workup
- temperaturecooled to 0° C.
- stirringThe reaction mixture is stirred for 3 hours at room temperature
- extractionextracted with ether
- washthe extract is washed with a saturated solution of NaCl
- dry with materialdried over Na2SO4
- concentrationconcentrated under vacuum
- customThe residue obtained
- customis purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-bc1a8910815e472c877fe9fe3d95695d
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05679693
Reaction notes
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