Sodium Hydroxide → ((S)-7-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

HRID 453771Notes

Reaction equation

HRID 453771 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:19][CH2:20][C@H:21]2[CH2:23][O:22]2)=[C:13]([O:15]C(=O)C)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:19][CH2:20][C@H:21]([CH2:23][OH:22])[O:15][C:13]=2[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86644717Acetic acid 5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

Product 1

HCID 66727448((S)-7-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of acetic acid 5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester (0.5 g, 1.59 mmol) in THF (10 ml) was added aq 2 M NaOH (1.04 ml). After stirring overnight at RT, THF was removed under reduced pressure and water (20 ml) was added. The water solution was then extracted two times with EtOAc. The combined organic layers washed with water and brine, dried (Na2SO4), and evaporated in vacuo. The crude product (0.45 g) was used without purification.

Workup

  1. customTHF was removed under reduced pressure and water (20 ml)
  2. additionwas added
  3. extractionThe water solution was then extracted two times with EtOAc
  4. washThe combined organic layers washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe crude product (0.45 g) was used without purification

Sources & evidence

ORD record
ord-e473e8b6364e49f691b53221efdaaf1f
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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