Sodium Hydroxide → ((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

HRID 2365972Notes

Reaction equation

HRID 2365972 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C(=O)C)=[C:11]([O:19][CH2:20][C@H:21]2[CH2:23][O:22]2)[CH:10]=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:14]=[CH:13][C:12]2[O:15][C@@H:21]([CH2:23][OH:22])[CH2:20][O:19][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86644714Acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

Product 1

HCID 66726995((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester (1.34 g, 4.26 mmol) in THF (30 ml), was added aq 2 M NaOH (2.45 ml). The mixture was stirred overnight at RT, THF was removed under reduced pressure and water (50 ml) was added. The water solution was then extracted three times with EtOAc and the combined extracts washed with water and brine. The organic layer was dried (Na2SO4), and evaporated in vacuo. The crude product (1.07 g) was used without purification.

Workup

  1. customTHF was removed under reduced pressure and water (50 ml)
  2. additionwas added
  3. extractionThe water solution was then extracted three times with EtOAc
  4. washthe combined extracts washed with water and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe crude product (1.07 g) was used without purification

Sources & evidence

ORD record
ord-88ff4682aa16416699902981fd0e2edc
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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