Hydrochloric Acid → (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanal
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].CC(C[AlH]CC(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
(1J.a) 9.2 g of t-butyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanoate are 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 DIBAH solution in toluene are then added dropwise within 1/2 hour in such as manner that the temperature does not exceed -70° C. The mixture is stirred at -75° C. for a further one hour. There are then added dropwise 7.4 ml of saturated ammonium chloride solution and subsequently 15.5 ml of 1N hydrochloric acid at -70° C. The cooling bath is removed and the mixture is left to warm to room temperature. After stirring at room temperature for one hour the organic phase is separated and washed with water. The organic phase is dried, filtered and evaporated. The material obtained is chromatographed on silica gel. There is obtained [(R)-3-[(tetrahydro-2H-pyran-2-yl)oxyl]tetradecanal as a colourless oil.
Workup
- customdoes not exceed -70° C
- customThe cooling bath is removed
- waitthe mixture is left
- temperatureto warm to room temperature
- stirringAfter stirring at room temperature for one hour the organic phase
- customis separated
- washwashed with water
- customThe organic phase is dried
- filtrationfiltered
- customevaporated
- customThe material obtained
- customis chromatographed on silica gel
Sources & evidence
- ORD record
- ord-7d1c028bb53e4cbca227ca28d9a605b3
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04983746
Reaction notes
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