Sodium metaborate → HCID 54065558, compound

HRID 264912

Reaction equation

HRID 264912 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-203cc9548934400e91597e87c78c9044
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Linked notes

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