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Sodium Hydroxide → 5-Chloro-2-[[(2S)-2-hydroxy-3-(trityloxy)propyl]oxy]benzonitrile

HRID 1160475
Notes
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Reaction equation

HRID 1160475 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11]([O:30][CH2:31][C@@H:32]1[CH2:34][O:33]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[K+].[OH-].[Na+]>C1(C)C=CC=CC=1.COCCOCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:34][C@H:32]([OH:33])[CH2:31][O:30][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:6]([CH:9]=1)[C:7]#[N:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 27774205-Chloro-2-hydroxybenzonitrileHCID 7168113(S)-Glycidyl Trityl EtherHCID 23665647Potassium tert-butoxide

Product 1

HCID 684202295-Chloro-2-[[(2S)-2-hydroxy-3-(trityloxy)propyl]oxy]benzonitrileYield 85%

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8150DiglymeSolvent

Conditions

Temperature
105 °C

Procedure

To a diglyme (1.1 L) solution of 5-chloro-2-hydroxybenzonitrile (the compound of Reference Example 1; 270 g, 1.8 mol) and (2S)-2-[(trityloxy)methyl]oxirane (465 g, 1.47 mol) was added potassium tert-butoxide (33 g, 0.29 mol) at room temperature, followed by stirring the reaction mixture at 105° C. for 23 hours. The reaction mixture was cooled with ice, to which toluene (2 L) and a 1N sodium hydroxide aqueous solution (1.35 L) were then added to separate an organic layer. The organic layer was washed 3 times each sequentially with the 1N sodium hydroxide aqueous solution (1.35 L) and warm water (3 L), followed by vacuum concentration. Toluene (3 L) was added to the concentrate, to dissolved it, followed by cooling and filtering the precipitated crystal to obtain 590 g of the title compound (yield: 85%).

Workup

  1. customto separate an organic layer
  2. washThe organic layer was washed 3 times each sequentially with the 1N sodium hydroxide aqueous solution (1.35 L)
  3. temperaturewarm water (3 L)
  4. concentrationfollowed by vacuum concentration
  5. additionToluene (3 L) was added to the concentrate
  6. dissolutionto dissolved it
  7. temperatureby cooling
  8. filtrationfiltering the precipitated crystal

Sources & evidence

ORD record
ord-94c1de99ff704bcd84489c6b27aafbdc
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816405B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes