HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

N-Methoxy-N-methylbenzamide → 1-Phenyl-3-[3-(4-(dimethylamino)benzyloxy)phenyl]-2-propyne-1-one

HRID 1757510
Notes
Print preview

Reaction equation

HRID 1757510 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][N:12]([CH3:29])[C:13]1[CH:28]=[CH:27][C:16]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([C:25]#[CH:26])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1.CON(C)[C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[C:34]1([C:33](=[O:40])[C:26]#[C:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH2:17][C:16]3[CH:27]=[CH:28][C:13]([N:12]([CH3:11])[CH3:29])=[CH:14][CH:15]=3)[CH:20]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 193882263-(4-(Dimethylamino)benzyloxy)phenylacetyleneHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 193882181-Phenyl-3-[3-(4-(dimethylamino)benzyloxy)phenyl]-2-propyne-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4-(dimethylamino)benzyloxy)phenylacetylene (0.51 g, 2 mmol) in tetrahydrofuran and stir the solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenzamide (0.4 g, 2.4 mmol), remove the cooling bath andstir at room temperature for 1 hour. Partition the mixture between ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Filter through silica gel and elute with 10% ethyl acetate/hexane to yield a crude solid. Purifyby silica gel chromatography to give the title compound. Alternatively, compounds of formula (1) can be prepared according to the procedure set forth in Scheme B, wherein all substituents, unless otherwise indicated, are previously described. ##STR3##

Workup

  1. customPartition the mixture between ethyl ether and water
  2. customseparate the organic phase
  3. dry with materialdry (MgSO4)
  4. filtrationFilter
  5. customevaporate the solvent in vacuo
  6. customto yield an oil
  7. filtrationFilter through silica gel
  8. washelute with 10% ethyl acetate/hexane
  9. customto yield a crude solid

Sources & evidence

ORD record
ord-811a5c27251840fcad575856719bd0b2
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05446068

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes