Sodium hydride → HCID 21109460, compound

HRID 270157

Reaction equation

HRID 270157 reaction equation
[H-].[Na+].[Cl-].[CH3:4][O:5][C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][C:7]=1[CH3:32].[O:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[O:39][CH2:40][C:41]1[N:42]=[C:43]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)[S:44][C:45]=1[CH:46]=O>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[CH3:4][O:5][C:6]1[CH:31]=[CH:30][C:9](/[CH:10]=[CH:46]/[C:45]2[S:44][C:43]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:56])([F:57])[F:55])=[CH:50][CH:49]=3)=[N:42][C:41]=2[CH2:40][O:39][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][O:33]2)=[CH:8][C:7]=1[CH3:32]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 211094534-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 461800353-Methyl-4-methoxybenzyl triphenylphosphonium chloride

Product 1

HCID 21109460HCID 21109460, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of NaH (60% dispersion in mineral oil, 242mg, 6.32mmoles, 1.4eq) in dry CH2Cl2(15ml) was added (4-Methoxy-3-methylbenzyl)(triphenyl)phosphonium chloride (2.62g, 6.32mmoles, 1.4eq). This was allowed to stir at room temperature for 1.5hours followed by the dropwise addition of 4-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (1.68g, 4.51mmoles, 1eq) in anhydrous carbon tetrachloride (25ml). The resulting reaction mixture was refluxed overnight at which point (after cooling to room temperature) the reaction washed with 1N NaOH, H2O, brine, dried over Na2SO4and concentrated in vacuo to yield a >100% yield of a light green oil. The crude material was used without purification.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed overnight at which point (after cooling to room temperature) the reaction
  3. washwashed with 1N NaOH, H2O, brine
  4. customdried over Na2SO4and
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f50d18a975a54beaae29fbd75c6198dd
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Linked notes

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