Methanol → {4-[2-(Benzyloxy)ethoxy]-3-tert-butoxyphenyl}methanol

HRID 591323Notes

Reaction equation

HRID 591323 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][C:15]=1[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.[Cl-].[NH4+]>C1COCC1>[CH2:3]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][C:15]=1[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 891562294-[2-(Benzyloxy)ethoxy]-3-tert-butoxybenzaldehyde

Product 1

HCID 70978543{4-[2-(Benzyloxy)ethoxy]-3-tert-butoxyphenyl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 1.00 g (26.5 mmol) sodium borohydride in 80 ml THF was added 2, 0.9 g (8.83 mmol) 4-[2-(benzyloxy)ethoxy]-3-tert-butoxybenzaldehyde diluted in 40 ml THF drop by drop. The reaction mixture was stirred for 10 min. Methanol (5.8 ml) was added to this mixture drop by drop. The reaction mixture was stirred for 2 hours and poured onto ˜200 ml stirred ice-cooled saturated aqueous ammonium chloride solution. The solution was extracted trice with dichloromethane. The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The crude product was used in the following reaction without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. additionpoured onto ˜200 ml
  3. stirringstirred ice-
  4. extractionThe solution was extracted trice with dichloromethane
  5. dry with materialThe combined organic phases were dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used in the following reaction without further purification

Sources & evidence

ORD record
ord-11d45f88025b4d879dc660c4ca8f9a5a
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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