Ethanol → 2-(4-Ethoxy-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 445578Notes

Reaction equation

HRID 445578 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[CH:4][C:3]=1[O:17][CH3:18].[C:19]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:20]=1.C(O)C.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.CCOC(C)=O>[CH2:19]([O:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:9][C:10]([CH3:12])([CH3:11])[C:13]([CH3:14])([CH3:15])[O:16]2)=[CH:4][C:3]=1[O:17][CH3:18])[CH3:20]

Participants

7

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 596200852-(4-Ethoxy-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-hydroxy-3-methoxyphenylboronic acid pinacol ester (Aldrich, Buchs, Switzerland, 200 mg, 0.800 mmol), triphenylphosphine (315 mg, 1.200 mmol) and ethanol (0.056 ml, 0.960 mmol) in THF (4 ml) under Argon was added dropwise diisopropyl azodicarboxylate (0.253 ml, 1.20 mmol). The RM was stirred at it for 17.5 h. Then the RM was diluted with EtOAc and the organic layer was washed with brine (2×), before being dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by MPLC (hexane/EtOAc 0 to 30%). The fractions containing product were together evaporated to give the title compound as a white solid. (HPLC: tR 3.58 min (Method A); M+H=279 MS-ES)

Workup

  1. washthe organic layer was washed with brine (2×)
  2. dry with materialbefore being dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was absorbed on silica gel
  6. custompurified by MPLC (hexane/EtOAc 0 to 30%)
  7. additionThe fractions containing product
  8. customwere together evaporated

Sources & evidence

ORD record
ord-9db6ea868d3947f69251bf8734d26126
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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