Ammonium Chloride → 1-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-ol

HRID 546857Notes

Reaction equation

HRID 546857 reaction equation
[CH2:1]([C:3]([C:22]1[CH:35]=[CH:34][C:25]([O:26][CH2:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:24]([CH3:36])[CH:23]=1)([C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[C:8]([CH3:21])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C:3]([C:22]1[CH:35]=[CH:34][C:25]([O:26][CH2:27][CH:28]([OH:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:24]([CH3:36])[CH:23]=1)([C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:13][C:14]([CH3:19])([CH3:20])[C:15]([CH3:17])([CH3:18])[O:16]2)=[C:8]([CH3:21])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3611392Lithium tri-s-butylborohydrideHCID 577089771-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one

Product 1

HCID 577089691-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-olYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one (Example 30-(2); 0.50 g, 1.02 mmol) in tetrahydrofuran (10 mL) was cooled to −78° C. A 1 M solution of L-selectride (R) in tetrahydrofuran (1.0 mL) was added dropwise, and the mixture was stirred for 20 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (5% ethyl acetate/hexane) to give the title compound (0.42 g, 83%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-84181990a5c24b2c9dc31b543f371b67
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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