Lithium borohydride → HCID 89649943, compound

HRID 1479032Notes

Reaction equation

HRID 1479032 reaction equation
[BH4-].[Li+].C[O:4][C:5](=O)[CH:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[O:16])[CH3:7]>O1CCOCC1>[OH:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH:6]([CH3:7])[CH2:5][OH:4]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 15732700140451-38-3

Product 1

HCID 89649943HCID 89649943, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Lithium borohydride (458 mg; 21 mmol; 3 eq.) was added to a solution of 2-(2-formyl-phenoxy)-propionic acid methyl ester (1.46 mg; 7 mmol; 1 eq.) in 1,4-dioxane (20 mL) and the resulting mixture was stirred at room temperature for 2 hours. After dilution with EA, the solution was washed with water, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (960 mg, 75%) as colourless oil. 1H NMR (DMSO-d6) δ 7.37-7.32 (m, 1H), 7.21-7.14 (m, 1H), 6.67 (d, J=8.3 Hz, 1H), 6.90 (dt, J=1.0, 7.4 Hz, 1H), 4.95 (t, J=5.7 Hz, 1H), 4.86 (t, J=5.7 Hz, 1H), 4.59-4.33 (m, 3H), 3.56-3.40 (m, 2H), 1.20 (d, J=6.2 Hz, 3H).

Workup

  1. washAfter dilution with EA, the solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c782b94144294f10b2950065d8e205f4
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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