(4S)-4-[2-(4-methoxyphenoxy)ethyl]-2,2-dimethyl-1,3-dioxolane → (2S)-4-(4-methoxyphenoxy)butane-1,2-diol

HRID 1012865Notes

Reaction equation

HRID 1012865 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][C@H:10]2[CH2:14][O:13]C(C)(C)[O:11]2)=[CH:5][CH:4]=1>CC(O)=O.O>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][C@H:10]([OH:11])[CH2:14][OH:13])=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 67319955(4S)-4-[2-(4-methoxyphenoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 67317445(2S)-4-(4-methoxyphenoxy)butane-1,2-diol

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of (4S)-4-[2-(4-methoxyphenoxy)ethyl]-2,2-dimethyl-1,3-dioxolane (8.2 g, 30.8 mmol) in AcOH/water was stirred at rt for 5 h and concentrated in vacuo. The residue was co-evaporated with toluene (3×) and then pumped under high vacuum to give the desired product. 1H NMR (400 MHz, Acetone-d6): δ7.28 (2 H, d), 6.91 (2 H, d), 4.43 (2 H, s), 3.80 (3 H, s), 3.77 (1H, m), 3.66-3.42 (5 H, m), 1.86-1.76 (1H, m), 1.68-1.60 (1H, m).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58fd7d7ff6524b04ac0e2e88c9340802
Source dataset
uspto-grants-2011_07
Patent number
USRE042562E1

Reaction notes

Loading…