Allyl Alcohol → HCID 86602453, compound

HRID 1455006Notes

Reaction equation

HRID 1455006 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([NH:12][C:13]1[C:18]([CH:19]=[O:20])=[C:17](Cl)[N:16]=[C:15]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=2[F:31])[N:14]=1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:32]([OH:35])[CH:33]=[CH2:34].[OH-].[Na+]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:32]([O:35][C:17]1[C:18]([CH:19]=[O:20])=[C:13]([NH:12][C@H:10]([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[N:14]=[C:15]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=2[F:31])[N:16]=1)[CH:33]=[CH2:34]

Participants

6

Reactant 3

HCID 7858Allyl AlcoholHCID 14798Sodium Hydroxide2×HCID 86602451HCID 86602451, compound

Product 1

HCID 86602453HCID 86602453, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

To the subtitle product of step ii) (1.0 g) in toluene was added allyl alcohol (0.23 g), sodium hydroxide (0.16 g) and benzyltriethylammonium chloride (10 mg). The mixture was stirred at room temperature for 2 h before sodium hydroxide solution (10 ml, 1M) was added the organics extracted with EtOAc (2×50 ml). The combined organics were washed with brine (20 ml) and dried (MgSO4). The solid was filtered and the filtrate evaporated to dryness to yield the subtitle compound as a white solid. Yield 1.0 g

Workup

  1. additionwas added the
  2. extractionorganics extracted with EtOAc (2×50 ml)
  3. washThe combined organics were washed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationThe solid was filtered
  6. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-0ced63389f194c8cb292e60530212048
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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