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

1,2-Dimethoxyethane → [4'-(Morpholin-4-yl)biphenyl-3-yl]methanol

HRID 1021214
Notes
Print preview

Reaction equation

HRID 1021214 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)O1.Br[C:29]1[CH:30]=[C:31]([CH2:35][OH:36])[CH:32]=[CH:33][CH:34]=1.COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:21]1([C:18]2[CH:17]=[CH:16][C:15]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][OH:36])[CH:30]=3)=[CH:20][CH:19]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 851413-Bromobenzyl alcoholHCID 27953614-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

Product 1

HCID 68308508[4'-(Morpholin-4-yl)biphenyl-3-yl]methanolYield 86.6%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis(triphenylphosphine)palladium (36 mg) and sodium carbonate (330 mg) were added to a mixture of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (300 mg), (3-bromophenyl)methanol (233 mg), DME (6 ml), and water (3 ml), followed by stirring at 80° C. overnight, and then the reaction mixture was concentrated under reduced pressure. Water and CHCl3 were added to the obtained residue, and the organic layer was dried over MgSO4, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane/CHCl3) to obtain [4′-(morpholin-4-yl)biphenyl-3-yl]methanol (242 mg).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater and CHCl3 were added to the obtained residue
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane/CHCl3)

Sources & evidence

ORD record
ord-79eb507037ee4b9fb8658186f41dedd3
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716470B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes