Hydrochloric Acid → (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanal

HRID 6055Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:9][C:10](OC(C)(C)C)=[O:11].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:9][CH:10]=[O:11]

Participants

Conditions

Temperature: -75 °C

Procedure

I)a) 9.2 g of t-butyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanoate were dissolved in 115 ml of toluene while gassing with argon and with the exclusion of moisture and cooled to -75° C. 26.5 ml of a 1.2M solution of diisobutylaluminum hydride in toluene were then added dropwise in such a manner that the temperature did not exceed -70° C. After stirring at -75° C. for 1 hour there were added dropwise 7.4 ml of saturated aqueous ammonium chloride solution and subsequently 15.5 ml of 1N hydrochloric acid at -70° C. The mixture was then left to warm to room temperature. After stirring for 1 hour the organic phase was dried, filtered and evaporated. The material obtained was chromatographed on silica gel. There was obtained (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanal as a colorless oil.

Workup

customdid not exceed -70° C
waitThe mixture was then left
temperatureto warm to room temperature
stirringAfter stirring for 1 hour the organic phase
customwas dried
filtrationfiltered
customevaporated
customThe material obtained
customwas chromatographed on silica gel

Sources & evidence

ORD record: ord-3076d3da99f84c1fb207661fe9054400
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246960

Reaction notes

Loading…