Hydrochloric Acid → HCID 14814227, compound

HRID 1089261Notes

Reaction equation

HRID 1089261 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([O:21]COC)[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([O:8][CH2:9][C@@H:10]([OH:21])[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14814224HCID 14814224, compound

Product 1

HCID 14814227HCID 14814227, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-1,4-dibenzyloxy-2-(methoxymethoxy)butane (2 g, 6 mmol) in methanol (14 ml) was added a 2% solution of methanolic hydrogen chloride (6 ml, 2.5 mmol). The solution was stirred at room temperature for 7 hours, the solvent removed and the residue chromatographed on silica eluting with ethyl acetate hexane 1:1 to give (S)-1,4-dibenzyloxy-2-hydroxybutane (1.46 g, 84%), [α]D25 -7.3° (c 1.1 in ethanol); IR: υmax (film) 3450, 3080, 3060, 3015, 2920, 2860, 2800, 1950, 1870, 1810, 1605, 1585, 1495, 1450, 1365, 1310, 1260, 1205, 1100, 1030, 1000, 950, 915, 820, 805, 760, 700, 610 cm-1 ; 1H NMR: δH (CDCl3) 1.79 (2H, d, t J=6 Hz and 6 Hz, CH2), 2.86 (1H, d, J=3 Hz, D2O exchangeable, OH), 3.45 (2H, m, CH2), 3.65 (2H, m, CH2), 4.05 (1H, m, CH), 4.51 (2H, s, CH2), 4.55 (2H, s, CH2), 7.3 (10H, m, 2×C6H5). Found: C, 75.64; H, 7.87%. C18H22O3 requires: C, 75.50; H, 7.74%.

Workup

  1. customthe solvent removed
  2. customthe residue chromatographed on silica eluting with ethyl acetate hexane 1:1

Sources & evidence

ORD record
ord-312d156ffb0946079f2bc9974c374f65
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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