Hydrochloric Acid → (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol

HRID 973341Notes

Reaction equation

HRID 973341 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH:11]=[O:12].[BH4-].[Na+].Cl>COCCOCCOC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86735173(4S)-4-(2-tetrahydropyranyloxy)nonanal

Product 1

HCID 68122110(4S)-4-(2-tetrahydropyranyloxy)-1-nonanol

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of (4S)-4-(2-tetrahydropyranyloxy)-nonanal (43.5 g., 0.18 mole) in diglyme (125 ml.) is treated with sodium borohydride (3.8 g., 0.10 mole). The temperature rises to 45° with the resulting exothermic reaction. The solution is stirred 4 hours, acidified with concentrated hydrochloric acid, and concentrated on the rotary evaporator. Water is added to the residue and the oily product is taken up in ether; washed with water and brine and dried over sodium sulfate. Evaporation of the ether leaves (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol as a colorless oil to be used in the next step without further purification.

Workup

  1. customThe temperature rises to 45° with the resulting exothermic reaction
  2. concentrationconcentrated on the rotary evaporator
  3. additionWater is added to the residue
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the ether

Sources & evidence

ORD record
ord-f138a4ba4bf14b0aba1cefc2085fa96e
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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