Pyridine → (S)-1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethanol

HRID 926198Notes

Reaction equation

HRID 926198 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[C@H:13]([OH:16])[CH2:14][OH:15].N1C=CC=CC=1.[C:23](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[C@H:13]([OH:16])[CH2:14][O:15][C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 67127139(S)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

Product 1

HCID 89676565(S)-1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (S)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol (6.70 grams, 28.2 mmol) and CH2Cl2 (67 mL) was treated with pyridine (4.78 mL, 59.2 mmol) at 23° C. Trityl chloride (8.28 g, 29.6 mmol) was added and the reaction was stirred for 24 h. The reaction was washed with 1.0 M aq CuSO4 monohydrate (3×50 mL), H2O (2×50 mL), and brine (50 mL). The final organic layer was dried over Na2SO4, filtered, and concentrated. The residue was treated with benzene and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give (S)-1-(1-chloro-3-methylnaphthalen-2-yl)-2-(trityloxy)ethanol. 1H NMR (400 MHz, CDCl3) δ 8.22 (d, J=8.2 Hz, 1H), 7.69 (d, J=8.2 Hz, 1H), 7.53-7.44 (m, 2H), 7.51 (s, 1H), 7.43-7.40 (m, 6H), 7.30-7.20 (m, 9H), 5.93-5.77 (m, broad, 1H), 3.59 (dd, J=9.4, 9.0 Hz, 1H), 3.52 (dd, J=9.4, 5.0 Hz, 1H), 2.85 (d, broad, J=4.3 Hz, 1H), 2.52 (s, 3H).

Workup

  1. washThe reaction was washed with 1.0 M aq CuSO4 monohydrate (3×50 mL), H2O (2×50 mL), and brine (50 mL)
  2. dry with materialThe final organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue was treated with benzene
  6. custompurified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-200428e9ff11450583287ff9843f10d4
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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