Water → (R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

HRID 926213Notes

Reaction equation

HRID 926213 reaction equation
CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.[OH2:59].[Cl:60][C:61]1[C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[CH:64]=[C:63]([CH3:71])[C:62]=1[CH:72]=[CH2:73]>C(O)(C)(C)C.C(OCC)(=O)C>[Cl:60][C:61]1[C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[CH:64]=[C:63]([CH3:71])[C:62]=1[C@@H:72]([OH:22])[CH2:73][OH:59]

Participants

6

Reactant 3

HCID 962WaterHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 671260761-Chloro-3-methyl-2-vinylnaphthalene

Product 1

HCID 89677395(R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A biphasic mixture of AD-mix-β (45.7 g, excess) in tert-butanol (147 mL)/H2O (147 mL) was cooled to 0° C. and 1-chloro-3-methyl-2-vinyl-naphthalene (4.46 g, 22.0 mmol) was added. The reaction mixture was stirred for 7 days at 0° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol. 1H-NMR: 400 MHz, (CDCl3) δ 8.27 (d, J=8.4 Hz, 1H), 7.73 (d, J=7.6 Hz, 1H), 7.57-7.50 (m, 3H), 5.70 (dd, J=10.0, 4.0 Hz, 1H), 4.11 (t, J=10.4 Hz, 1H), 3.79 (dd, J=11.6, 4.0 Hz, 1H), 2.66 (s, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-484df3b9cca04ec5a9b00d0a267f0a2b
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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