Sodium metaborate → HCID 54065558, compound

HRID 744801

Reaction equation

HRID 744801 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][CH2:20][O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B([O-])=O.[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][CH2:20][O:21][CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 145326Sodium metaborateHCID 214586084-(Benzyloxy)-3-(3-methoxypropoxy)benzaldehyde

Product 1

HCID 54065558HCID 54065558, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 31 g of 4-benzyloxy-3-(3-methoxypropyloxy)-benzaldehyde in 530 ml of ethanol/water=8:2 is added dropwise to a suspension, stirred at 0° C., of 11.74 g of sodium boranate in 530 ml of a mixture of ethanol/water=8:2. The reaction mixture is stirred for one hour at 0° C. and is then concentrated by evaporation. The residue is partitioned between diethyl ether and water. The combined organic phases are dried over sodium sulfate and concentrated by evaporation, and the residue is purified by FC (100 g of silica gel, dichloromethane/diethyl ether=1:1), yielding the title compound: Rf (dichloromethane/diethyl ether=1:1)=0.43.

Workup

  1. concentrationis then concentrated by evaporation
  2. customThe residue is partitioned between diethyl ether and water
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customthe residue is purified by FC (100 g of silica gel, dichloromethane/diethyl ether=1:1)

Sources & evidence

ORD record
ord-185bc328f40542908d5a6b0f96ed9c7c
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Linked notes

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