Sodium borohydride → HCID 59602216, compound

HRID 1631848Notes

Reaction equation

HRID 1631848 reaction equation
[CH2:1]1[C:5]2([CH2:14][CH2:13][CH2:12][C:7]3([CH2:11][CH2:10][CH2:9][CH2:8]3)[C:6]2=[O:15])[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[CH2:18]1[C:22]2(CCCC3(CCCC3)[CH:23]2[OH:32])[CH2:21]CC1>[OH-].[Na+].C1(C)C=CC=CC=1.O1CCCC1.O.CO>[C:23]([O:15][CH:6]1[C:5]2([CH2:1][CH2:2][CH2:3][CH2:4]2)[CH2:14][CH2:13][CH2:12][C:7]21[CH2:11][CH2:10][CH2:9][CH2:8]2)(=[O:32])[C:22]([CH3:18])=[CH2:21]

Participants

9

Reactant 3

HCID 4311764Sodium borohydrideHCID 21675006HCID 21675006, compoundHCID 59602221HCID 59602221, compound

Product 1

HCID 59602216HCID 59602216, compoundYield 99%

Reagents, catalysts & solvents 5

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

With stirring under nitrogen atmosphere under ice cooling, 80 g of dispiro[4.1.4.3]tetradecan-6-one and 73 g of tetrahydrofuran were added to a mixture of 14.5 g of sodium borohydride, 145 g of methanol, 0.3 g of 25% sodium hydroxide aqueous solution, 8 g of water, and 73 g of tetrahydrofuran. The reaction mixture was stirred overnight at room temperature, and 300 ml of toluene was added thereto, whereupon the organic layer was separated. Through ordinary work-up of extraction, washing and drying, and subsequent concentration under reduced pressure, there was obtained 81.0 g (yield 99%) of the target compound, dispiro[4.1.4.3]-tetradecan-6-ol. This compound had a purity high enough to use in the subsequent step without further purification.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customwhereupon the organic layer was separated
  3. extractionThrough ordinary work-up of extraction
  4. washwashing
  5. customdrying
  6. concentrationsubsequent concentration under reduced pressure

Sources & evidence

ORD record
ord-9ad4d7de664b4493af8d57a8a8afe78d
Source dataset
uspto-grants-2014_07
Patent number
US08791288B2

Reaction notes

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