Hydrochloric Acid → HCID 20479585, compound

HRID 1649358Notes

Reaction equation

HRID 1649358 reaction equation
[CH3:1][Si:2]([CH3:20])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].Cl>O1CCCC1.ClCCl>[CH3:20][Si:2]([CH3:1])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9855836Potassium sodium tartarateHCID 129427045-[Decyl(dimethyl)silyl]pentanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 20479585HCID 20479585, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen, 17.1 g (56.9 mmol) of 6,6-dimethyl-6-sila-n-hexadecanoic acid, dissolved in 20 ml of absolute tetrahydrofuran, is added dropwise to 5.4 g (142 mmol) of lithium aluminum hydride in 150 ml of absolute tetrahydrofuran (caution being exercised due to hydrogen evolution). The resultant mixture is stirred at 60° for 18 hrs., then cooled to about 10°; and injected into a cold (about 10°) saturated aqueous of sodium-potassium tartrate. Dichloromethane is added and the mixture acidified with dilute hydrochloric acid (2 N). The organic phase is separated, washed with saturated aqueous sodium bicarbonate solution, then dried over anh. sodium sulfate, filtered and the filtrate concentrated to obtain the crude title product of this step as an oily residue. The oily residue is distilled in a kugelrohr apparatus and the fraction collecting at 108° to 115° and 0.19 to 0.13 mm Hg to obtain refined title product of this step.

Workup

  1. temperature, then cooled to about 10°
  2. customThe organic phase is separated
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anh. sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customto obtain the crude title product of this step as an oily residue
  8. distillationThe oily residue is distilled in a kugelrohr apparatus
  9. customthe fraction collecting at 108° to 115°

Sources & evidence

ORD record
ord-6459c892ba8c43e99cf6b262b1f8d6ee
Source dataset
uspto-grants-1983_11
Patent number
US04416876

Reaction notes

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