2,2-Dimethoxypropane → HCID 67086997, compound

HRID 1665105Notes

Reaction equation

HRID 1665105 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C@@H:12]([OH:15])[CH2:13][OH:14])=[CH:8][CH:7]=1.CO[C:20](OC)([CH3:22])[CH3:21].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C1COCC1>[CH3:21][C:20]1([CH3:22])[O:15][C@H:12]([CH2:11][O:10][C:9]2[CH:16]=[CH:17][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:7][CH:8]=2)[CH2:13][O:14]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67087064HCID 67087064, compound

Product 1

HCID 67086997HCID 67086997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (S)-3-[4-(4-Hydroxy-butyl)-phenoxy]-propane-1,2-diol (43 g, 179 mmol) in THF (700 ml) is added 2,2-dimethoxypropane (94 ml, 760 mmol) followed by PPTS (4.5 g, 17.9 mmol). The resultant mixture is stirred at room temperature overnight. The solution is concentrated in vacuo and the residue taken up in DCM (500 ml). This is washed with water, dried (MgSO4) and concentrated in vacuo. The residue is purified through a silica plug (300 g) eluting with 10% followed by 25% EtOAc/iso-hexanes. The desired fractions are concentrated to give 4-[4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-butan-1-ol as a clear oil; 1H NMR (CDCl3): 1.42, (3H, s), 1.48 (3H, s), 1.53-1.73 (4H, m), 2.20 (1H, t, J=2.5 Hz), 2.60 (2H, t, J=7.2 Hz), 3.68 (2H, t, J=6.4 Hz), 3.92 (2H, dt, J=5.8 and 8.5 Hz), 4.07 (1H, dd, J=5.4 and 9.5 Hz), 4.19 (1H, dd, J=6.4 and 8.5 Hz), 4.49 (1H, p, J=5.7 Hz), 6.85 (2H, d, J=8.7 Hz), 7.11 (2H, d, J=8.7 Hz).

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. washThis is washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified through a silica plug (300 g)
  6. washeluting with 10%
  7. concentrationThe desired fractions are concentrated

Sources & evidence

ORD record
ord-d74d0d2ecbfb45a68ba13b6996d51abd
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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