Hydrochloric Acid → HCID 21412035, compound

HRID 2071668Notes

Reaction equation

HRID 2071668 reaction equation
[O:1]=[C:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH:5]1[O:9][CH:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:7][CH2:6]1.[CH3:25][Si](C)(C)N[Si](C)(C)C.C[Si](C)(C)Cl.C[Mg]Br.Cl>CCOCC.N1C=CC=CC=1>[OH:1][C:2]([CH3:25])([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH:5]1[O:9][CH:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:7][CH2:6]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 21412029HCID 21412029, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21412035HCID 21412035, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

IX (6.30 g, 0.0185 mole), hexamethyldisilazane (HMDS) (12 ml), trimethylchlorosilane (TMCS) (6 ml), and pyridine (40 ml) were mixed and kept overnight at room temperature. The resulting white suspension was evaporated to dryness (50° C, 10 mm Hg). Ether (100 ml) was added, and the suspension was filtered. The resulting clear, yellow solution of X was cooled to 0° C, and methylmagnesium bromide in ether (3.8N, 8.0 ml, 0.030 mole) was added dropwise during 20 minutes. After stirring for 2 hours at room temperature, the white suspension being formed was poured into a mixture of cold hydrochloric acid (0.25N, 140 ml) and ether (50 ml). The ethereal phase was separated, and the aqueous layer was extracted with ether (50 + 25 ml). The combined ethereal extracts were washed with water 50 ml) and dried over sodium sulfate. The solvent was removed from a water bath (60° C, 10 mm Hg), and the residual light yellowish oil (7.40 g) was distilled under reduced pressure to give 5.40 g (82%) of XI as a light yellowish oil, b0.08 203°-210° C, nD25 1.4710.

Workup

  1. customThe resulting white suspension was evaporated to dryness (50° C, 10 mm Hg)
  2. additionEther (100 ml) was added
  3. filtrationthe suspension was filtered
  4. customthe white suspension being formed
  5. customThe ethereal phase was separated
  6. extractionthe aqueous layer was extracted with ether (50 + 25 ml)
  7. washThe combined ethereal extracts were washed with water 50 ml) and
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed from a water bath (60° C, 10 mm Hg)
  10. distillationthe residual light yellowish oil (7.40 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-c14a1c68776745128cbad8e99ef4d897
Source dataset
uspto-grants-1977_09
Patent number
US04048198

Reaction notes

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