Ammonium Chloride → beta(R)-benzyloxy-alpha(RS)-phenyl-1,4-dioxaspiro[4,5]decane-2(R)-ethanol

HRID 376005Notes

Reaction equation

[CH2:1]([O:8][C@@H:9]([C@H:12]1[CH2:16][O:15][C:14]2([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:13]1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([Mg]Cl)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH2:1]([O:8][C@@H:9]([C@H:12]1[CH2:16][O:15][C:14]2([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:13]1)[CH:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of 4.30 g (0.015 mmol) of α(S)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-acetaldehyde in 50 ml of anhydrous diethyl ether was cooled to -8° C. and 15 ml of a 2M solution of phenylmagnesium chloride in tetrahydrofuran were added dropwise over a period of 1 hour. The mixture was stirred at -5° C. for 2 hours, then allowed to warm to room temperature and poured into 50 ml of 10% ammonium chloride solution. The mixture was extracted twice with 100 ml of ethyl acetate each time. The ethyl acetate extracts were dried over anhydrous magnesium sulphate and evaporated. The residue was subjected to flash chromatography on silica gel using 5% methanol in dichloromethane for the elution. There were obtained 2.47 g of β(R)-benzyloxy-α(RS)-phenyl-1,4-dioxaspiro[4,5]decane-2(R)-ethanol in the form of a colourless gum; MS (C.I.): m/e 369 [M+H]+.

Workup

temperatureto warm to room temperature
extractionThe mixture was extracted twice with 100 ml of ethyl acetate each time
dry with materialThe ethyl acetate extracts were dried over anhydrous magnesium sulphate
customevaporated
washThe residue was subjected to flash chromatography on silica gel using 5% methanol in dichloromethane for the elution

Sources & evidence

ORD record: ord-36ba96c85f274e85b2dd314a3c03b28f
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488115

Reaction notes

Loading…