Sodium Hydroxide → HCID 86720733, compound

HRID 512921Notes

Reaction equation

HRID 512921 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21](/[CH:25]=[CH:26]/[C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][C:31]([Cl:37])=[CH:32][CH:33]=3)[N:28]=2)[CH:20]=1)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].[OH-].[Na+]>O1CCOCC1>[Cl:37][C:31]1[CH:30]=[C:29]2[C:34]([CH:35]=[CH:36][C:27](/[CH:26]=[CH:25]/[C:21]3[CH:20]=[C:19]([C:12]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])[CH2:11][CH2:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:38])=[O:2])[CH:24]=[CH:23][CH:22]=3)=[N:28]2)=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86720734HCID 86720734, compound

Product 1

HCID 86720733HCID 86720733, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of Ketal-ester 42 (0.65 g, 1.29 mmol) in 1,4-dioxane (10.0 ml) was added a solution of Sodium hydroxide (0.6 g, 15 mmol). The reaction mixture was heated at 80° C. for 18 hours. The resulting mixture was concentrated to remove dioxane, diluted with water (25 ml) and acidify with acetic acid, followed by usual workup with dichloromethane and FC to give (Ib.96) (0.35 g, 55%).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customto remove dioxane
  3. additiondiluted with water (25 ml)
  4. customto give (Ib.96) (0.35 g, 55%)

Sources & evidence

ORD record
ord-8e52d0282508465b883a072dd90fab8a
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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