Propan-2-ol--water (1/1) → (S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate

HRID 2271397Notes

Reaction equation

HRID 2271397 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=C(C=C)[CH:14]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:27][CH:28]([OH:30])[CH3:29].[OH2:31]>>[OH:30][C@@H:28]([C:29]1[CH:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:25]=[CH:26][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:8][CH:9]=2)[N:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=1)[CH2:27][OH:31]

Participants

3

Reactant 2

HCID 21889133Propan-2-ol--water (1/1)HCID 66666565Methyl 6-(4-(4-fluorophenoxy)phenyl)-4-vinylpicolinate

Product 1

HCID 66668464(S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate

Procedure

To a suspension of methyl 6-(4-(4-fluorophenoxy)phenyl)-4-vinylpicolinate (0.309 g, 0.884 mmol) in 10 mL 1:1 iPrOH/H2O was added AD-Mix α (1.205 g). The reaction was stirred for 3 h then partitioned between 50 mL EtOAc and 25 mL water. The organics were separated, dried over MgSO4, filtered, and concentrated in vacuo to give crude (S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate which was used in the next step without further purification (LC/MS: m/z=384.1 [M+H]+).

Workup

  1. additionwas added AD-Mix α (1.205 g)
  2. customthen partitioned between 50 mL EtOAc and 25 mL water
  3. customThe organics were separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c83b1d92c2c5446e85a18097b59b4e3b
Source dataset
uspto-grants-2015_09
Patent number
US09120752B2

Reaction notes

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